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

Thomas Di Franco; Nicolas Boutin; Xile Hu

doi:10.1055/s-0033-1338544

Synthesis, Table of Contents

Synthesis 2013; 45(21): 2949-2958
DOI: 10.1055/s-0033-1338544

feature article

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

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Abstract

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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.

Key words

cross coupling - nickel - alkyl halides - pincer complex - Suzuki–Miyaura coupling

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References

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