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

Francisco González-Bobes and Gregory C. Fu*

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

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

DOI: 10.1021/ja0613761

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Abstract

Suzuki cross-coupling reactions of an unprecedented array of unactivated primary and secondary alkyl halides with arylboronic acids can be accomplished through the use of nickel/amino alcohol-based catalysts. Both the nickel precatalysts and the amino alcohols are commcercially available and air-stable.

see article for more examples

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

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

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.

Room-Temperature Hiyama Cross-Couplings of Arylsilanes with Alkyl Bromides and Iodides

J.-Y. Lee, G. C. Fu, J. Am. Chem. Soc., 2003, 125, 5616-5617.

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Key Words

Suzuki Coupling, Substituted Arenes

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ID: J48-Y2006-1980