Alkyl-Alkyl Suzuki Cross-Couplings of Unactivated Secondary Alkyl Halides at Room Temperature

Bunnai Saito and Gregory C. Fu*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, Email: gcfmit.edu

B. Saito, G. C. Fu, J. Am. Chem. Soc., 2007, 129, 9602-9603.

DOI: 10.1021/ja074008l

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Abstract

Commercially available trans-N,N‘-dimethyl-1,2-cyclohexanediamine serves as an effective ligand for Ni-catalyzed Suzuki cross-couplings of unactivated alkyl electrophiles with alkylboranes at room temperature. Earlier success in Suzuki couplings of such electrophiles had been restricted to reactions with aryl- and vinylboron reagents at elevated temperature.

see article for more examples

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Amino Alcohols as Ligands for Nickel-Catalyzed Suzuki Reactions of Unactivated Alkyl Halides, Including Secondary Alkyl Chlorides, with Arylboronic Acids

F. González-Bobes, G. C. Fu, J. Am. Chem. Soc., 2006, 128, 5360-5361.

Boronic Acids: New Coupling Partners in Room-Temperature Suzuki Reactions of Alkyl Bromides. Crystallographic Characterization of an Oxidative-Addition Adduct Generated under Remarkably Mild Conditions

J. H. Kirchhoff, M. R. Netherton, I. D. Hill, G. C. Fu, J. Am. Chem. Soc., 2002, 124, 13662-13663.

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Key Words

Suzuki Coupling

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ID: J48-Y2007-2670