GREGORY FUSummaryAffiliation: Massachusetts Institute of Technology Country: USA Publications
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Publications
Cross-couplings of alkyl electrophiles under "ligandless" conditions: Negishi reactions of organozirconium reagentsSheryl L Wiskur
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 126:82-3. 2004....
The development of versatile methods for palladium-catalyzed coupling reactions of aryl electrophiles through the use of P(t-Bu)3 and PCy3 as ligandsGregory C Fu
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA
Acc Chem Res 41:1555-64. 2008..These methods have been applied in a wide array of settings, such as natural-product synthesis, materials science, and bioorganic chemistry...- From the design of a chiral Lewis acid catalyst to metal-catalyzed coupling reactionsGregory C Fu
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Org Chem 69:3245-9. 2004..In this perspective, I describe my group's nonobvious path from an interest in chiral Lewis acid catalysis to a project focused on the development of new palladium and nickel catalysts for carbon-carbon bond-forming reactions... - Applications of planar-chiral heterocycles as ligands in asymmetric catalysisGregory C Fu
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
Acc Chem Res 39:853-60. 2006..Thus, planar-chiral heterocycles furnish high enantioselectivity in a variety of processes, including isomerizations of allylic alcohols, O-H insertions, and 1,3-dipolar cycloadditions... - A versatile method for Suzuki cross-coupling reactions of nitrogen heterocyclesNoriaki Kudo
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
Angew Chem Int Ed Engl 45:1282-4. 2006 - Ligands for palladium-catalyzed cross-couplings of alkyl halides: use of an alkyldiaminophosphane expands the scope of the Stille reactionHaifeng Tang
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
Angew Chem Int Ed Engl 42:5079-82. 2003 
Nickel-catalyzed asymmetric negishi cross-couplings of secondary allylic chlorides with alkylzincsSunghee Son
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 130:2756-7. 2008..The method has been applied in two key steps of a formal total synthesis of fluvirucinine A1...- Nickel-catalyzed cross-couplings of organosilicon reagents with unactivated secondary alkyl bromidesDavid A Powell
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 126:7788-9. 2004..Noteworthy attributes of the method are its scope (secondary electrophiles), its high functional-group compatibility, and the air stability of the catalyst components... - Enantioselective alkenylation via nickel-catalyzed cross-coupling with organozirconium reagentsSha Lou
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 132:5010-1. 2010.... - Catalytic asymmetric Hiyama cross-couplings of racemic alpha-bromo estersXing Dai
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 130:3302-3. 2008 - Intramolecular Heck reactions of unactivated alkyl halidesLuke Firmansjah
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 129:11340-1. 2007 - Asymmetric nickel-catalyzed Negishi cross-couplings of secondary alpha-bromo amides with organozinc reagentsChristian Fischer
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
J Am Chem Soc 127:4594-5. 2005..The process tolerates a variety of functional groups and affords the desired product in good yield and in high enantiomeric excess... - Boronic acids: new coupling partners in room-temperature Suzuki reactions of alkyl bromides. Crystallographic characterization of an oxidative-addition adduct generated under remarkably mild conditionsJan H Kirchhoff
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 124:13662-3. 2002..The resulting adduct is sufficiently stable toward beta-hydride elimination that it can be structurally characterized, and it is a chemically competent intermediate in the cross-coupling process... - Synthesis of functionalized cyclopentenes through catalytic asymmetric [3+2] cycloadditions of allenes with enonesJonathan E Wilson
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
Angew Chem Int Ed Engl 45:1426-9. 2006 - Suzuki cross-couplings of unactivated secondary alkyl bromides and iodidesJianrong Zhou
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 126:1340-1. 2004..The ability to couple readily available, easy-to-handle boronic acids is an attractive feature of this catalyst system... - Asymmetric synthesis of highly substituted beta-lactones by nucleophile-catalyzed [2+2] cycloadditions of disubstituted ketenes with aldehydesJonathan E Wilson
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
Angew Chem Int Ed Engl 43:6358-60. 2004 - Catalytic asymmetric Staudinger reactions to form beta-lactams: an unanticipated dependence of diastereoselectivity on the choice of the nitrogen substituentElaine C Lee
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 127:11586-7. 2005..Along with serving as interesting targets in their own right, N-triflyl beta-lactams readily react with nucleophiles to generate useful families of compounds, such as gamma-amino alcohols and beta-amino acids... - Umpolung of Michael acceptors catalyzed by N-heterocyclic carbenesChristian Fischer
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 128:1472-3. 2006..In this process, the nucleophilic catalyst transiently transforms the normally electrophilic beta carbon into a nucleophilic site through an unanticipated addition-tautomerization sequence... - Room-temperature Stille cross-couplings of alkenyltin reagents and functionalized alkyl bromides that possess beta hydrogensKarsten Menzel
Department of Chemistry, Massachusetts Institute of Technology, Cambridge 02139, USA
J Am Chem Soc 125:3718-9. 2003..The structure of the phosphine (P(t-Bu)2Me) is well suited for facilitating oxidative addition and avoiding beta-hydride elimination, while the fluoride serves to activate the tin reagent for efficient transmetalation... - Pd/P(t-Bu)(3): a mild and general catalyst for Stille reactions of aryl chlorides and aryl bromidesAdam F Littke
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 124:6343-8. 2002..Pd/P(t-Bu)(3) also functions as an active catalyst for Stille reactions of aryl bromides, furnishing the first general method for room-temperature cross-couplings... - Phosphine-catalyzed formation of carbon-sulfur bonds: catalytic asymmetric synthesis of gamma-thioestersJianwei Sun
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 132:4568-9. 2010..The phosphine catalyst of choice, TangPhos, had previously only been employed as a chiral ligand for transition metals, not as an efficient enantioselective nucleophilic catalyst... - Palladium-catalyzed coupling reactions of aryl chloridesAdam F Littke
Massachusetts Institute of Technology, Department of Chemistry, 77 Massachusetts Avenue, Room 18-411, Cambridge 02139-4307, USA
Angew Chem Int Ed Engl 41:4176-211. 2002..This review summarizes both the seminal early work and the exciting recent developments in the area of palladium-catalyzed couplings of aryl chlorides... - Catalytic asymmetric cycloaddition of ketenes and nitroso compounds: enantioselective synthesis of alpha-hydroxycarboxylic acid derivativesMaximilian Dochnahl
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
Angew Chem Int Ed Engl 48:2391-3. 2009..In addition to serving as potentially bioactive target molecules, the products can be transformed into other important classes of compounds, such as alpha-hydroxycarboxylic acid derivatives... - Amino alcohols as ligands for nickel-catalyzed suzuki reactions of unactivated alkyl halides, including secondary alkyl chlorides, with arylboronic acidsFrancisco González-Bobes
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 128:5360-1. 2006..In view of the remarkable diversity of amino alcohols that are readily accessible, this discovery may open the door to the rapid development of versatile catalysts for a wide range of cross-coupling processes... - Phosphine-catalyzed enantioselective synthesis of oxygen heterocyclesYing Kit Chung
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
Angew Chem Int Ed Engl 48:2225-7. 2009..This method provides a new approach to the enantioselective synthesis of tetrahydrofurans, tetrahydropyrans, and dihydrobenzopyrans... - Cross-couplings of unactivated secondary alkyl halides: room-temperature nickel-catalyzed Negishi reactions of alkyl bromides and iodidesJianrong Steve Zhou
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
J Am Chem Soc 125:14726-7. 2003..This communication describes a simple catalyst system-Ni(cod)2/s-Bu-Pybox-that achieves room-temperature Negishi reactions of an array of functionalized primary and secondary alkyl bromides and iodides... - A new copper-catalyzed [3 + 2] cycloaddition: enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocyclesRyo Shintani
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 125:10778-9. 2003..Through the use of a chiral phosphaferrocene-oxazoline ligand, a wide range of substrates can be coupled to generate useful heterocycles in very good enantiomeric excess... - Enantioselective alkyl-alkyl Suzuki cross-couplings of unactivated homobenzylic halidesBunnai Saito
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 130:6694-5. 2008..To the best of our knowledge, there are no previous examples of enantioselective Suzuki couplings of alkyl electrophiles (activated or unactivated). Both of the catalyst components are commercially available... - Enantioselective synthesis of protected amines by the catalytic asymmetric addition of hydrazoic acid to ketenesXing Dai
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
Angew Chem Int Ed Engl 46:4367-9. 2007 - Nickel/bis(oxazoline)-catalyzed asymmetric Kumada reactions of alkyl electrophiles: cross-couplings of racemic alpha-bromoketonesSha Lou
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 132:1264-6. 2010..Third, readily available bis(oxazolines) are shown for the first time to be effective ligands for cross-couplings of alkyl electrophiles, thereby opening the door to new opportunities in asymmetric catalysis... - Kinetic resolutions of indolines by a nonenzymatic acylation catalystForrest O Arp
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 128:14264-5. 2006..This work provides a rare example of a nonenzyme-based acylation catalyst for the kinetic resolution of amines... - Catalytic asymmetric synthesis of tertiary alkyl chloridesElaine C Lee
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
Angew Chem Int Ed Engl 46:977-9. 2007 - Alkyl-alkyl suzuki cross-couplings of unactivated secondary alkyl halides at room temperatureBunnai Saito
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 129:9602-3. 2007 - Nickel-catalyzed asymmetric cross-couplings of racemic propargylic halides with arylzinc reagentsSean W Smith
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 130:12645-7. 2008..From a practical point of view, it is noteworthy that the catalyst components (NiCl2.glyme and pybox ligand 1) are commercially available... - Hiyama reactions of activated and unactivated secondary alkyl halides catalyzed by a nickel/norephedrine complexNeil A Strotman
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
Angew Chem Int Ed Engl 46:3556-8. 2007 - Catalytic enantioselective synthesis of beta-lactams: intramolecular Kinugasa reactions and interception of an intermediate in the reaction cascadeRyo Shintani
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
Angew Chem Int Ed Engl 42:4082-5. 2003 - Room-temperature Hiyama cross-couplings of arylsilanes with alkyl bromides and iodidesJae-Young Lee
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 125:5616-7. 2003..The first method for achieving Hiyama couplings of unactivated alkyl bromides and iodides is reported. The desired carbon-carbon bond formation proceeds under mild conditions (room temperature) with good functional-group tolerance... - Toward an improved understanding of the unusual reactivity of Pd0/trialkylphosphane catalysts in cross-couplings of alkyl electrophiles: quantifying the factors that determine the rate of oxidative additionIvory D Hills
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
Angew Chem Int Ed Engl 42:5749-52. 2003 - Elucidating reactivity differences in palladium-catalyzed coupling processes: the chemistry of palladium hydridesIvory D Hills
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 126:13178-9. 2004.... - Palladium-catalyzed negishi cross-coupling reactions of unactivated alkyl iodides, bromides, chlorides, and tosylatesJianrong Zhou
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 125:12527-30. 2003..The process is compatible with a variety of functional groups, including esters, amides, imides, nitriles, and heterocycles... - Copper-catalyzed asymmetric N-H insertion reactions: couplings of diazo compounds with carbamates to generate alpha-amino acidsElaine C Lee
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 129:12066-7. 2007 - Suzuki cross-couplings of alkyl tosylates that possess beta hydrogen atoms: synthetic and mechanistic studiesMatthew R Netherton
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
Angew Chem Int Ed Engl 41:3910-2. 2002 - Enantioselective addition of amines to ketenes catalyzed by a planar-chiral derivative of PPY: possible intervention of chiral Brønsted-acid catalysisBrian L Hodous
Department of Chemistry, Massachusetts Institute of Technology, Cambridge 02139, USA
J Am Chem Soc 124:10006-7. 2002..On the basis of mechanistic studies, it is suggested that the planar-chiral catalyst plays an unanticipated role in this process as a chiral Brønsted acid... - Catalytic enantioselective Negishi reactions of racemic secondary benzylic halidesForrest O Arp
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 127:10482-3. 2005..The method has been applied to the catalytic enantioselective synthesis of intermediates employed by others in the generation of bioactive compounds (e.g., trikentrin A and an androgen receptor agonist)... - Catalytic enantioselective synthesis of quaternary stereocenters via intermolecular C-acylation of silyl ketene acetals: dual activation of the electrophile and the nucleophileAra H Mermerian
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 125:4050-1. 2003..Mechanistic studies support the hypothesis that the reaction involves activation both of the silyl ketene acetal (generation of an enolate) and of the anhydride (formation of an acylpyridinium ion)... - Cu(I)/bis(azaferrocene)-catalyzed enantioselective synthesis of beta-lactams via couplings of alkynes with nitronesMichael M-C Lo
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 124:4572-3. 2002..Appealing attributes of this process include the ready availability of the starting materials, the functional-group tolerance of the reaction, and the convergency of the approach... - Enantioselective Staudinger synthesis of beta-lactams catalyzed by a planar-chiral nucleophileBrian L Hodous
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 124:1578-9. 2002.... - Catalytic enantioselective O-H insertion reactionsThomas C Maier
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 128:4594-5. 2006..Specifically, a copper/bisazaferrocene catalyst couples alcohols such as 2-trimethylsilylethanol with alpha-aryl-alpha-diazo esters in high yield and good ee... - Asymmetric alkyl-alkyl cross-couplings of unactivated secondary alkyl electrophiles: stereoconvergent Suzuki reactions of racemic acylated halohydrinsNathan A Owston
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 132:11908-9. 2010..A range of protected bromohydrins, as well as a protected chlorohydrin and a homologated bromohydrin, are coupled in good ee by a catalyst derived from commercially available components... - Nucleophile-catalyzed asymmetric acylations of silyl ketene imines: application to the enantioselective synthesis of verapamilAra H Mermerian
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
Angew Chem Int Ed Engl 44:949-52. 2005 - Stille cross-couplings of unactivated secondary alkyl halides using monoorganotin reagentsDavid A Powell
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 127:510-1. 2005..The method employs easily handled and inexpensive catalyst components (NiCl2 and 2,2'-bipyridine) and, through the use of monoorganotin reagents, avoids the formation of toxic and difficult-to-remove triorganotin side products... - Catalytic enantioselective construction of all-carbon quaternary stereocenters: synthetic and mechanistic studies of the C-acylation of silyl ketene acetalsAra H Mermerian
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 127:5604-7. 2005..Mechanistic studies provide strong support for a catalytic cycle that involves activation of both the electrophile (anhydride --> acylpyridinium) and the nucleophile (silyl ketene acetal --> enolate)... - Catalytic asymmetric couplings of ketenes with aldehydes to generate enol estersCarsten Schaefer
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
Angew Chem Int Ed Engl 44:4606-8. 2005 - Copper-catalyzed asymmetric [4+1] cycloadditions of enones with diazo compounds to form dihydrofuransSunghee Son
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 129:1046-7. 2007 - Catalytic asymmetric synthesis of esters from ketenesSheryl L Wiskur
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 127:6176-7. 2005..The product aryl esters can be converted into useful derivatives, such as enantioenriched alcohols and carboxylic acids... - Asymmetric Suzuki cross-couplings of activated secondary alkyl electrophiles: arylations of racemic alpha-chloroamidesPamela M Lundin
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 132:11027-9. 2010.... - Asymmetric carbon-carbon bond formation gamma to a carbonyl group: phosphine-catalyzed addition of nitromethane to allenesSean W Smith
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 131:14231-3. 2009..This strategy provides an attractive method for the catalytic asymmetric gamma functionalization of carbonyl (and related) compounds... - The first applications of carbene ligands in cross-couplings of alkyl electrophiles: sonogashira reactions of unactivated alkyl bromides and iodidesMatthias Eckhardt
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA
J Am Chem Soc 125:13642-3. 2003.... - Enantioselective nucleophilic catalysis: the synthesis of aza-beta-lactams through [2+2] cycloadditions of ketenes with azo compoundsJacob M Berlin
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
Angew Chem Int Ed Engl 47:7048-50. 2008
Research Grants
- Asymmetric Nucleophilic CatalysisGregory C Fu; Fiscal Year: 2010..This proposal is directed at addressing both of these challenges. ..
- Asymmetric Catalysis by Transition MetalsGREGORY FU; Fiscal Year: 2006..the application of these new ligands to the development of highly enantioselective transition metal-catalyzed reactions. ..
- DEVELOPMENT OF ENANTIOSELECTIVE NUCLEOPHILIC CATALYSTSGREGORY FU; Fiscal Year: 2006..and (2) the development of enantioselective processes catalyzed by these planar-chiral catalysts. It is anticipated that useful new methods for stereoselective organic synthesis will emerge from this investigation. ..
- Asymmetric Nucleophilic CatalysisGREGORY FU; Fiscal Year: 2007..Enantioselective catalysis, the focus of this research program, is a particularly attractive strategy for achieving this objective. ..
- Asymmetric Nucleophilic CatalysisGREGORY FU; Fiscal Year: 2009..Enantioselective catalysis, the focus of this research program, is a particularly attractive strategy for achieving this objective. ..
- Asymmetric Nucleophilic CatalysisGregory C Fu; Fiscal Year: 2010..This proposal is directed at addressing both of these challenges. ..
- Palladium- and Nickel-Catalyzed C-C Bond FormationGREGORY FU; Fiscal Year: 2009..Mechanistic studies will play an important role in this project, since an improved understanding of metal-based reactivity should greatly facilitate catalyst development. ..
- DEVELOPMENT OF ENANTIOSELECTIVE NUCLEOPHILIC CATALYSTSGREGORY FU; Fiscal Year: 2001..It is anticipated that useful new methods for stereoselective organic synthesis will emerge from this investigation. ..
- Versatile Methods for Palladium-Catalyzed CouplingsGREGORY FU; Fiscal Year: 2004....