Agilent 5973 GC/MS System

Summary

Principal Investigator: GARY MOLANDER
Abstract: Advances in biomedical research funded by the NIH in our department require ready access to combined gas chromatography/mass spectrometry (GC/MS) for routine analyses. Currently supported projects that would benefit from a new GC/MS include: 1) Studies geared toward the development of new synthetic methods for selective organic synthesis. 2) Programs involved in the synthesis of structurally complex molecules of biological interest. 3) Synthesis of new ligands for both early and late transition metal complexes and the examination of the properties and reactivity of the resulting metal-ligand adducts as applied to the selective synthesis of organic molecules. 4) Mechanistic studies of charge transfer reactions as well as the biomimetic chemistry of light harvesting and small molecule activation. 5) Synthetic studies directed toward the design and synthesis of new antimalarials, and the synthesis of ingenol, a potent activator of the cell signaling system protein kinase C. A critical need for the successful and timely development of these diverse projects is access to an instrument for obtaining GC/MS data on a user-friendly, routine basis. Our current lack of such instrumentation negatively affects the ability to carry out many of these studies. This critical capability, in the form of an instrument for everyday analysis, is urgently needed.
Funding Period: 2002-05-01 - 2003-04-30
more information: NIH RePORT

Top Publications

  1. pmc Synthesis and applications of α-trifluoromethylated alkylboron compounds
    O Andreea Argintaru
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104 6323 USA
    Angew Chem Int Ed Engl 52:13656-60. 2013
  2. pmc Potassium Boc-protected secondary aminomethyltrifluoroborates: synthesis and Suzuki-Miyaura cross-coupling reactions
    Gary A Molander
    Roy and Diana A Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    Org Lett 14:4458-61. 2012
  3. pmc Oxidative condensations to form benzimidazole-substituted potassium organotrifluoroborates
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, United States
    Org Lett 14:4242-5. 2012
  4. pmc Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    J Am Chem Soc 134:11667-73. 2012
  5. pmc Suzuki-Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborate with aryl and hetaryl mesylates
    Gary A Molander
    Roy and Diana A Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    Org Lett 14:3138-41. 2012
  6. pmc Synthesis of amidomethyltrifluoroborates and their use in cross-coupling reactions
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, United States
    Org Lett 12:4876-9. 2010
  7. pmc Reinvestigation of aminomethyltrifluoroborates and their application in Suzuki-Miyaura cross-coupling reactions
    Jessica Raushel
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, United States
    J Org Chem 76:2762-9. 2011
  8. pmc Nickel-catalyzed cross-coupling of potassium aryl- and heteroaryltrifluoroborates with unactivated alkyl halides
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104 6323, USA
    Org Lett 12:5783-5. 2010
  9. pmc Palladium-catalyzed, direct boronic acid synthesis from aryl chlorides: a simplified route to diverse boronate ester derivatives
    Gary A Molander
    Roy and Diana Vagelos Laboratories and Penn Merck Laboratory for High Throughput Experimentation, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, United States
    J Am Chem Soc 132:17701-3. 2010
  10. pmc Direct alkylation of heteroaryls using potassium alkyl- and alkoxymethyltrifluoroborates
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, United States
    Org Lett 13:1852-5. 2011

Scientific Experts

  • GARY MOLANDER
  • Spencer D Dreher
  • Marc Presset
  • Nicolas Fleury-Brégeot
  • Frederik Rombouts
  • Daniel Oehlrich
  • Deidre L Sandrock
  • O Andreea Argintaru
  • Brittany A Tschaen
  • Jessica Raushel
  • Young Ae Cho
  • Andrea Dorfleutner
  • Jason R Schmink
  • Ioana Aron
  • Daweon Ryu
  • Virginie Colombel
  • Floriane Beaumard
  • Deborah Pakyz
  • Kanth V Josyula
  • Ludivine Jean-Gérard
  • Cheng yi Chen
  • Dong Su Kim
  • Hong Ryul Ahn
  • Jungyeob Ham
  • Belgin Canturk
  • Youngjin Cho
  • Scott A Weed
  • Deanne Vincent
  • Daniel C Flynn
  • Jess Cunnick
  • Hong Lin
  • Christian Stehlik

Detail Information

Publications61

  1. pmc Synthesis and applications of α-trifluoromethylated alkylboron compounds
    O Andreea Argintaru
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104 6323 USA
    Angew Chem Int Ed Engl 52:13656-60. 2013
    ..These substrates represent the first isolated α-trifluoromethylated alkylboron building blocks, and these reagents lead to a variety of useful bench-stable, synthetic intermediates. Pin=pinacol. ..
  2. pmc Potassium Boc-protected secondary aminomethyltrifluoroborates: synthesis and Suzuki-Miyaura cross-coupling reactions
    Gary A Molander
    Roy and Diana A Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    Org Lett 14:4458-61. 2012
    ....
  3. pmc Oxidative condensations to form benzimidazole-substituted potassium organotrifluoroborates
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, United States
    Org Lett 14:4242-5. 2012
    ..The method allows the facile preparation of benzimidazole-containing triaromatic products in two steps from simple potassium formyl substituted aryl- or heteroaryltrifluoroborates...
  4. pmc Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    J Am Chem Soc 134:11667-73. 2012
    ..For ease of isolation and to preserve the often sensitive C-B bond, all boronic acids were readily converted to their more stable trifluoroborate counterparts...
  5. pmc Suzuki-Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborate with aryl and hetaryl mesylates
    Gary A Molander
    Roy and Diana A Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    Org Lett 14:3138-41. 2012
    ....
  6. pmc Synthesis of amidomethyltrifluoroborates and their use in cross-coupling reactions
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, United States
    Org Lett 12:4876-9. 2010
    ..Amidomethyltrifluoroborates were successfully synthesized in a one-pot fashion and used in cross-coupling reactions with a wide variety of aryl and heteroaryl chlorides...
  7. pmc Reinvestigation of aminomethyltrifluoroborates and their application in Suzuki-Miyaura cross-coupling reactions
    Jessica Raushel
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, United States
    J Org Chem 76:2762-9. 2011
    ..Minor adjustments to the previously disclosed reaction conditions are reported that permit a similar level of activity as nucleophiles in Suzuki-Miyaura cross-coupling reactions...
  8. pmc Nickel-catalyzed cross-coupling of potassium aryl- and heteroaryltrifluoroborates with unactivated alkyl halides
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104 6323, USA
    Org Lett 12:5783-5. 2010
    ..Several functional groups were tolerated on both the electrophilic and the nucleophilic partners. Chemoselective reactivity of C(sp(3))-Br bonds in the presence of C(sp(2))-Br bonds was achieved...
  9. pmc Palladium-catalyzed, direct boronic acid synthesis from aryl chlorides: a simplified route to diverse boronate ester derivatives
    Gary A Molander
    Roy and Diana Vagelos Laboratories and Penn Merck Laboratory for High Throughput Experimentation, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, United States
    J Am Chem Soc 132:17701-3. 2010
    ..Further, the intermediate boronic acids can be easily converted to a wide range of useful boronates. Finally, a two-step, one-pot method was developed to couple two aryl chlorides efficiently in a Suzuki-Miyaura-type reaction...
  10. pmc Direct alkylation of heteroaryls using potassium alkyl- and alkoxymethyltrifluoroborates
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, United States
    Org Lett 13:1852-5. 2011
    ..This method leads to the synthesis of complex substituted heterocycles, which have been obtained with yields up to 89%...
  11. pmc Cross-coupling of mesylated phenol derivatives with potassium ammonio- and amidomethyltrifluoroborates
    Gary A Molander
    Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    Org Lett 13:1242-5. 2011
    ....
  12. pmc Palladium-catalyzed borylation of aryl and heteroaryl halides utilizing tetrakis(dimethylamino)diboron: one step greener
    Gary A Molander
    Roy and Diana Vagelos Laboratories and Penn Merck Laboratory for High Throughput Experimentation, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    Org Lett 14:4814-7. 2012
    ..Because tetrakis(dimethylamino)diboron is the synthetic precursor to both BBA and bis(pinacolato)diboron (B(2)Pin(2)), the new method represents a more atom-economical and efficient approach to current borylation methods...
  13. pmc Scope of the two-step, one-pot palladium-catalyzed borylation/Suzuki cross-coupling reaction utilizing bis-boronic acid
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, United States
    J Org Chem 77:8678-88. 2012
    ..The method also allows an efficient two-step, one-pot synthesis, providing access to three distinct cross-coupled products after column chromatography. The method also provides a rapid and convenient route to teraryl compounds...
  14. pmc Stereospecific cross-coupling of secondary organotrifluoroborates: potassium 1-(benzyloxy)alkyltrifluoroborates
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Penn Merck Laboratory for High Throughput Experimentation, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104 6323, USA
    J Am Chem Soc 134:16856-68. 2012
    ..This cross-coupling is stereospecific with complete retention of stereochemistry...
  15. pmc Pd-catalyzed alkynylation of 2-chloroacetates and 2-chloroacetamides with potassium alkynyltrifluoroborates
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104 6323, United States
    Org Lett 15:5052-5. 2013
    ..Propargyl esters and amides were obtained in high yields using a low catalyst loading, and the substrate scope of the reaction has been significantly improved over previous methods. ..
  16. pmc Suzuki-Miyaura cross-coupling of potassium trifluoro(N-methylheteroaryl)borates with aryl and heteroaryl halides
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    J Org Chem 78:6648-56. 2013
    ....
  17. pmc Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4]
    Gary A Molander
    Roy and Diana Vagelos Laboratories and Penn Merck Laboratory for High Throughput Experimentation, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    J Org Chem 78:6427-39. 2013
    ..To the best of our knowledge, the examples presented here represent the only effective Ni-catalyzed Miyaura borylations conducted at room temperature. ..
  18. pmc Pd-catalyzed cross-coupling of potassium alkenyltrifluoroborates with 2-chloroacetates and 2-chloroacetamides
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104 6323, USA
    Org Lett 15:3342-5. 2013
    ....
  19. pmc Pd-catalyzed Suzuki-Miyaura cross-coupling reactions between sulfamates and potassium Boc-protected aminomethyltrifluoroborates
    Gary A Molander
    Roy and Diana A Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, United States
    Org Lett 15:2534-7. 2013
    ..A broad range of substrates was successfully coupled to provide the desired products. Complex molecules containing a new carbon-carbon bond and an aminomethyl moiety could be prepared through this developed method. ..
  20. pmc Synthesis and minisci reactions of organotrifluoroborato building blocks
    Marc Presset
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, United States
    J Org Chem 78:4615-9. 2013
    ..Representative Minisci reactions are reported for select examples...
  21. pmc Synthesis and cross-coupling of sulfonamidomethyltrifluoroborates
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, United States
    Org Lett 13:1694-7. 2011
    ....
  22. pmc Suzuki-Miyaura cross-coupling of potassium alkoxyethyltrifluoroborates: access to aryl/heteroarylethyloxy motifs
    Nicolas Fleury-Brégeot
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    J Org Chem 77:10399-408. 2012
    ....
  23. pmc Pd-catalyzed aldehyde to ester conversion: a hydrogen transfer approach
    Brittany A Tschaen
    Roy and Diana A Vagelos Laboratories and Penn Merck Laboratory for High Throughput Experimentation, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    Org Lett 15:500-3. 2013
    ..This approach utilizes a hydrogen transfer protocol: concomitant reduction of acetone to isopropanol provides an inexpensive and sustainable approach that mitigates the need for other oxidants...
  24. pmc Suzuki-Miyaura cross-coupling of potassium dioxolanylethyltrifluoroborate and aryl/heteroaryl chlorides
    Nicolas Fleury-Brégeot
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, United States
    Org Lett 15:1536-9. 2013
    ..Copper-catalyzed borylation of 2-(2-bromoethyl)-1,3-dioxolane with bis(pinacolato)diboron followed by treatment with potassium bifluoride provides the key organotrifluoroborate reagent...
  25. pmc Palladium-catalyzed α-arylation of 2-chloroacetates and 2-chloroacetamides
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104 6323, USA
    J Org Chem 78:4123-31. 2013
    ..Utilization of organotrifluoroborate salts as nucleophilic partners allows a variety of functional groups and heterocyclic compounds to be tolerated...
  26. pmc Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: preparation and use of 4-trifluoroboratotetrahydroisoquinolones
    Marc Presset
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, United States
    Org Lett 15:1528-31. 2013
    ..These new boron-containing building blocks were derivatized by N-arylations, retaining the boron substituent for further elaboration...
  27. pmc Copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    Org Lett 13:4684-7. 2011
    ..Primary, secondary, and tertiary α,β-unsaturated amides are converted to the corresponding β-trifluoroboratoamides in good to excellent yields. The β-boration of a variety of α,β-unsaturated esters and ketones is also reported...
  28. pmc Nitrosation of aryl and heteroaryltrifluoroborates with nitrosonium tetrafluoroborate
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104 6323, USA
    J Org Chem 77:4402-13. 2012
    ..Aryl- and heteroaryltrifluoroborates were converted into the corresponding nitroso products in good to excellent yields. This method proved to be tolerant of a broad range of functional groups...
  29. pmc Cross-coupling of mesylated phenol derivatives with potassium alkoxymethyltrifluoroborates
    Gary A Molander
    Roy and Diana A Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    Org Lett 13:3948-51. 2011
    ..The corresponding aryl and heteroaryl alkoxymethyl compounds have been obtained with equal facility with both electron-rich and electron-poor substituents on the activated alcohol...
  30. pmc Synthesis and Suzuki-Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborate with aryl and hetaryl halides
    Gary A Molander
    Roy and Diana A Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    Org Lett 13:3956-9. 2011
    ..With this trifluoroborate, Suzuki-Miyaura cross-coupling reactions were investigated with a variety of both aryl and hetaryl chlorides in good to excellent yields...
  31. pmc Cross-coupling of mesylated phenol derivatives with potassium cyclopropyltrifluoroborate
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, United States
    J Org Chem 76:8126-30. 2011
    ..Both electron-enriched and electron-deficient aryl mesylates are suitable electrophilic partners for the Suzuki-Miyaura reaction. The scope was successfully extended to heteroaryl mesylates with yields up to 94%...
  32. pmc Metal-free chlorodeboronation of organotrifluoroborates
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    J Org Chem 76:7195-203. 2011
    ..Aryl-, heteroaryl-, alkenyl-, alkynyl-, and alkyltrifluoroborates were converted into the corresponding chlorinated products in good yields. This method proved to be tolerant of a broad range of functional groups...
  33. pmc Oxidation of organotrifluoroborates via oxone
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, United States
    J Org Chem 76:623-30. 2011
    ..This method proved to be tolerant of a broad range of functional groups, and in secondary alkyl substrates it was demonstrated to be completely stereospecific...
  34. pmc Use of potassium beta-trifluoroborato amides in Suzuki-Miyaura cross-coupling reactions
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    J Org Chem 74:5446-50. 2009
    ....
  35. pmc Condensation reactions to form oxazoline-substituted potassium organotrifluoroborates
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    Org Lett 11:3830-3. 2009
    ..The method allows the facile preparation of oxazole-containing triaromatic products in two steps from simple potassium formyl-substituted aryl- or heteroaryltrifluoroborates...
  36. pmc Organotrifluoroborates and monocoordinated palladium complexes as catalysts--a perfect combination for Suzuki-Miyaura coupling
    Gary A Molander
    Department of Chemistry, University of Pennsylvania, 231 S 34th Street, Philadelphia, PA 19104 6323, USA
    Angew Chem Int Ed Engl 48:9240-61. 2009
    ..In combination, these two components prove to be extraordinarily powerful partners for cross-coupling reactions...
  37. pmc Synthesis of an acyltrifluoroborate and its fusion with azides to form amides
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    J Org Chem 75:4304-6. 2010
    ..A uniquely stable acyl potassium trifluoroborate, potassium (2-phenylacetyl)trifluoroborate, has been synthesized and isolated. In the presence of an activating Lewis acid, this reagent reacts with azides to form amides in good yields...
  38. pmc Nickel-catalyzed C-O activation of phenol derivatives with potassium heteroaryltrifluoroborates
    Gary A Molander
    Roy and Diana A Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    Org Lett 12:4022-5. 2010
    ..A large number of heterobiaryls can be easily obtained with yields up to 99% using methanesulfonate cross-coupling partners...
  39. pmc Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides
    Gary A Molander
    Roy and Diana A Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    Org Lett 12:4384-7. 2010
    ..Moreover, the diastereoselectivities were preserved throughout the Suzuki-Miyaura cross-coupling reactions...
  40. pmc Stereospecific cross-coupling of secondary alkyl β-trifluoroboratoamides
    Deidre L Sandrock
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104 6323, USA
    J Am Chem Soc 132:17108-10. 2010
    ..The high selectivity toward product formation over an undesired β-H elimination pathway is achieved via an intramolecular coordination of an ancillary carbonyl to the metal center in the diorganopalladium intermediate...
  41. pmc Beta-aminoethyltrifluoroborates: efficient aminoethylations via Suzuki-Miyaura cross-coupling
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    Org Lett 9:203-6. 2007
    ..The potassium beta-aminoethyltrifluoroborates were easily prepared via hydroboration of enamine and enamide precursors. [reaction: see text]...
  42. pmc Suzuki-Miyaura cross-coupling reactions of potassium vinyltrifluoroborate with aryl and heteroaryl electrophiles
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    J Org Chem 71:9681-6. 2006
    ..Moderate to good yields are obtained in the presence of a variety of functional groups...
  43. pmc Suzuki-Miyaura cross-coupling reactions of benzyl halides with potassium aryltrifluoroborates
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    J Org Chem 71:9198-202. 2006
    ..The increased stability of potassium aryltrifluoroborates compared to other boron coupling partners makes this an effective route to functionalized methylene-linked biaryl systems...
  44. pmc Linchpin synthons: metalation of aryl bromides bearing a potassium trifluoroborate moiety
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    J Org Chem 71:7491-3. 2006
    ..Esters were unfortunately found to be unreactive...
  45. pmc Synthesis of functionalized organotrifluoroborates via the 1,3-dipolar cycloaddition of azides
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, 19104 6323, USA
    Org Lett 8:2767-70. 2006
    ..This method was then developed into a facile one-pot synthesis for the preparation of various organo-[1,2,3]-triazol-1-yl-trifluoroborates using haloalkyltrifluoroborates as the starting materials...
  46. pmc Synthesis of functionalized organotrifluoroborates via halomethyltrifluoroborates
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, 19104 6323, USA
    Org Lett 8:2031-4. 2006
    ..Moreover, a new synthetic method for the preparation of potassium organotrifluoroborates through nucleophilic substitution of the halide in these potassium halomethyltrifluoroborates is described...
  47. pmc One-pot synthesis of trisubstituted conjugated dienes via sequential Suzuki-Miyaura cross-coupling with alkenyl- and alkyltrifluoroborates
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    J Org Chem 71:2493-8. 2006
    ..Moreover, the method is operationally very simple because the organotrifluoroborates are stable in air, and the byproducts are innocuous inorganic salts...
  48. pmc Palladium(0)-catalyzed synthesis of chiral ene-allenes using alkenyl trifluoroborates
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    J Org Chem 71:1563-8. 2006
    ..Di-, tri-, and tetrasubstituted allenes were synthesized in moderate to high optical yields. Several racemic allenes possessing various functional groups were also synthesized...
  49. pmc Construction of bicyclic ring systems via a transannular SmI2-mediated ketone-olefin cyclization strategy
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104 6323, USA
    J Org Chem 72:1755-64. 2007
    ..These results demonstrate the efficiency and the potential of the transannular cyclization tactic for the creation of bicyclic ring systems...
  50. pmc Aminomethylations via cross-coupling of potassium organotrifluoroborates with aryl bromides
    Gary A Molander
    Roy and Diana A Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    Org Lett 9:1597-600. 2007
    ....
  51. pmc Preparation of potassium azidoaryltrifluoroborates and their cross-coupling with aryl halides
    Young Ae Cho
    Korea Institute of Science and Technology, 290 Daejeon dong, Gangneung 210 340, Korea
    Org Lett 11:4330-3. 2009
    ..Also, we successfully cross-coupled the azido-functionalized organotrifluoroborates and carried out a one-pot sequential cross-coupling/1,3-dipolar cycloaddition and a one-pot cross-coupling/azide reduction process...
  52. pmc Suzuki-Miyaura cross-coupling reactions of primary alkyltrifluoroborates with aryl chlorides
    Spencer D Dreher
    Department of Process Research and the Catalytic Reactions Discovery and Development Laboratory, Merck and Co, Inc, Rahway, New Jersey, USA
    J Org Chem 74:3626-31. 2009
    ....
  53. pmc Scope of the Suzuki-Miyaura cross-coupling reaction of potassium trifluoroboratoketohomoenolates
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    J Org Chem 74:1297-303. 2009
    ..These organoboron reagents were effectively cross-coupled with various aryl and heteroaryl chlorides...
  54. pmc Scope of the Suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    J Org Chem 74:973-80. 2009
    ..The cross-coupled products were obtained in good to excellent yields. This method represents an efficient and facile installation of heterocyclic building blocks onto preexisting organic substructures...
  55. pmc Orthogonal reactivity in boryl-substituted organotrifluoroborates
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104 6323, USA
    J Am Chem Soc 130:15792-3. 2008
    ..The stability of the trifluoroborate moiety to these conditions allows simple and efficient strategies for complex molecule construction...
  56. pmc Cross-coupling of cyclopropyl- and cyclobutyltrifluoroborates with aryl and heteroaryl chlorides
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104 6323, USA
    J Org Chem 73:7481-5. 2008
    ..Both of these secondary alkyl trifluoroborates coupled in moderate to excellent yield with electron-rich, electron-poor, and hindered aryl chlorides to give a variety of substituted aryl cyclopropanes and cyclobutanes...
  57. pmc Efficient cross-coupling of secondary alkyltrifluoroborates with aryl chlorides--reaction discovery using parallel microscale experimentation
    Spencer D Dreher
    Department of Process Research and the Catalytic Reactions Discovery and Development Laboratory, Merck and Co Inc, 126 East Lincoln Avenue, Rahway, New Jersey 07065, USA
    J Am Chem Soc 130:9257-9. 2008
    ..A ligand-dependent beta-hydride elimination/reinsertion mechanism was implicated in the cross-coupling of more hindered substrates, leading to isomeric mixtures of coupled products in some cases...
  58. ncbi Phosphorylation of AFAP-110 affects podosome lifespan in A7r5 cells
    Andrea Dorfleutner
    The Mary Babb Randolph Cancer Center and Department of Microbiology, Immunology and Cell Biology, West Virginia University, Morgantown, WV 26506 9300, USA
    J Cell Sci 121:2394-405. 2008
    ..Therefore, we hypothesize that AFAP-110 phosphorylation and/or dephosphorylation is involved in the regulation of podosome stability and lifespan...
  59. pmc cis-dihydroxylation of unsaturated potassium alkyl- and aryltrifluoroborates
    Gary A Molander
    Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, 19104 6323, USA
    Org Lett 8:75-8. 2006
    ..The resulting diols are efficient coupling partners in Suzuki-Miyaura-type reactions with both alkenyl and aryl bromides...