Stille coupling via C–N bond cleavage

Dong-Yu Wang, Masatoshi Kawahata, Ze-Kun Yang, Kazunori Miyamoto, Shinsuke Komagawa, Kentaro Yamaguchi (), Chao Wang () and Masanobu Uchiyama ()
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Dong-Yu Wang: Graduate School of Pharmaceutical Sciences, University of Tokyo
Masatoshi Kawahata: Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University
Ze-Kun Yang: Graduate School of Pharmaceutical Sciences, University of Tokyo
Kazunori Miyamoto: Graduate School of Pharmaceutical Sciences, University of Tokyo
Shinsuke Komagawa: Graduate School of Pharmaceutical Sciences, Osaka University
Kentaro Yamaguchi: Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University
Chao Wang: Graduate School of Pharmaceutical Sciences, University of Tokyo
Masanobu Uchiyama: Graduate School of Pharmaceutical Sciences, University of Tokyo

Nature Communications, 2016, vol. 7, issue 1, 1-9

Abstract: Abstract Cross-coupling is a fundamental reaction in the synthesis of functional molecules, and has been widely applied, for example, to phenols, anilines, alcohols, amines and their derivatives. Here we report the Ni-catalysed Stille cross-coupling reaction of quaternary ammonium salts via C–N bond cleavage. Aryl/alkyl-trimethylammonium salts [Ar/R–NMe3]+ react smoothly with arylstannanes in 1:1 molar ratio in the presence of a catalytic amount of commercially available Ni(cod)2 and imidazole ligand together with 3.0 equivalents of CsF, affording the corresponding biaryl with broad functional group compatibility. The reaction pathway, including C–N bond cleavage step, is proposed based on the experimental and computational findings, as well as isolation and single-crystal X-ray diffraction analysis of Ni-containing intermediates. This reaction should be widely applicable for transformation of amines/quaternary ammonium salts into multi-aromatics.

Date: 2016
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DOI: 10.1038/ncomms12937

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