Synthesis 2013; 45(21): 2949-2958
DOI: 10.1055/s-0033-1338544
feature article
© Georg Thieme Verlag Stuttgart · New York

Suzuki–Miyaura Cross-Coupling Reactions of Unactivated Alkyl Halides Catalyzed by a Nickel Pincer Complex

Thomas Di Franco
Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), ISIC-LSCI, BCH 3305, Lausanne 1015, Switzerland   Fax: +41(21)6939305   Email: xile.hu@epfl.ch
,
Nicolas Boutin
Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), ISIC-LSCI, BCH 3305, Lausanne 1015, Switzerland   Fax: +41(21)6939305   Email: xile.hu@epfl.ch
,
Xile Hu*
Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), ISIC-LSCI, BCH 3305, Lausanne 1015, Switzerland   Fax: +41(21)6939305   Email: xile.hu@epfl.ch
› Author Affiliations
Further Information

Publication History

Received: 04 September 2013

Accepted after revision: 13 September 2013

Publication Date:
27 September 2013 (online)


Abstract

A nickel(II) pincer complex, [(MeN2N)Ni-Cl], was used to catalyze alkyl–alkyl and alkyl–aryl Suzuki–Miyaura coupling reactions of unactivated alkyl halides. The coupling of 9-alkyl-9-bo­rabicyclo[3.3.1]nonane and 9-phenyl-9-borabicyclo[3.3.1]nonane reagents with alkyl halides was achieved in modest to good yields. The reactions tolerated a variety of useful functional groups including ester, ether, furan, thioether, acetal, and Boc groups.

Supporting Information

 
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