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
J. Am. Chem. Soc., 2006, 128 (16), pp 5360–5361
DOI: 10.1021/ja0613761
Publication Date (Web): April 1, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, gcf@mit.edu

Abstract

Abstract Image

Suzuki cross-coupling reactions of an unprecedented array of unactivated primary and secondary alkyl halides (including challenging alkyl chlorides) can be accomplished through the use of nickel/amino alcohol-based catalysts. Both the nickel precatalyst and the amino alcohols (prolinol or trans-2-aminocyclohexanol) are commercially available and air-stable. 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.

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History

  • Published In Issue April 26, 2006
  • Received February 27, 2006

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