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

J. Am. Chem. Soc., 128 (16), 5360 -5361, 2006. 10.1021/ja0613761 S0002-7863(06)01376-X
Web Release Date: April 1, 2006

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

Francisco Gonzlez-Bobes and Gregory C. Fu*

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139

gcf@mit.edu

Received February 27, 2006

Abstract:

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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