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The First Negishi Cross-Coupling Reaction of Two Alkyl Centers Utilizing a Pd−N-Heterocyclic Carbene (NHC) Catalyst†
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Section:Abstract
The development of an NHC-based system capable of cross-coupling sp3−sp3 centers in high yield has been a long-standing challenge. This communication describes the use of a Pd−NHC catalytic system that achieves room-temperature Negishi cross-couplings of unactivated, primary bromides and alkyl organozinc reagents with a variety of functionality.
Citing Articles
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This article has been cited by 24 ACS Journal articles (5 most recent appear below).
How Racemic Secondary Alkyl Electrophiles Proceed to Enantioselective Products in Negishi Cross-Coupling Reactions
Xufeng Lin, Jian Sun, Yanyan Xi, and Delian LinOrganometallics2011 Article ASAPHow Racemic Secondary Alkyl Electrophiles Proceed to Enantioselective Products in Negishi Cross-Coupling Reactions
Xufeng Lin, Jian Sun, Yanyan Xi, and Delian LinOrganometallics2011 Article ASAPTwo mechanisms, namely, the Ni(0)–Ni(II) and Ni(I)–Ni(III) mechanisms, for nickel-bis(oxazolinyl)pyridine complex catalyzed Negishi cross-coupling reaction were investigated with density functional calculations. The Ni(I)–Ni(III) mechanism, containing ...
A Structure–Activity Study of Ni-Catalyzed Alkyl–Alkyl Kumada Coupling. Improved Catalysts for Coupling of Secondary Alkyl Halides
Peng Ren, Oleg Vechorkin, Kim von Allmen, Rosario Scopelliti, and Xile HuJournal of the American Chemical Society2011 Article ASAPA Structure–Activity Study of Ni-Catalyzed Alkyl–Alkyl Kumada Coupling. Improved Catalysts for Coupling of Secondary Alkyl Halides
Peng Ren, Oleg Vechorkin, Kim von Allmen, Rosario Scopelliti, and Xile HuJournal of the American Chemical Society2011 Article ASAPA structure–activity study was carried out for Ni catalyzed alkyl–alkyl Kumada-type cross coupling reactions. A series of new nickel(II) complexes including those with tridentate pincer bis(amino)amide ligands (RN2N) and those with bidentate mixed amino-...
Nickel-Catalyzed Cross-Couplings Involving Carbon−Oxygen Bonds
Brad M. Rosen, Kyle W. Quasdorf, Daniella A. Wilson, Na Zhang, Ana-Maria Resmerita, Neil K. Garg, and Virgil PercecChemical Reviews2011 111 (3), 1346-1416Nickel-Catalyzed Cross-Couplings Involving Carbon−Oxygen Bonds
Brad M. Rosen, Kyle W. Quasdorf, Daniella A. Wilson, Na Zhang, Ana-Maria Resmerita, Neil K. Garg, and Virgil PercecChemical Reviews2011 111 (3), 1346-1416
Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners
Ranjan Jana, Tejas P. Pathak, and Matthew S. SigmanChemical Reviews2011 111 (3), 1417-1492Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners
Ranjan Jana, Tejas P. Pathak, and Matthew S. SigmanChemical Reviews2011 111 (3), 1417-1492
Copper-Catalyzed N-Allenylation of Allylic Sulfonamides
Andreas K. Å. Persson, Eric V. Johnston and Jan-E. BäckvallOrganic Letters2009 11 (17), 3814-3817Copper-Catalyzed N-Allenylation of Allylic Sulfonamides
Andreas K. Å. Persson, Eric V. Johnston and Jan-E. BäckvallOrganic Letters2009 11 (17), 3814-3817Allylic allenic amides have been synthesized via a copper-catalyzed cross-coupling between allylic sulfonamides and bromoallenes in moderate to good yields. Copper(I) thiophene-2-carboxylate (CuTC) was used a source of copper with DMEDA as the ligand. ...
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History
- Published In Issue August 18, 2005
- Received June 25, 2005
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