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Issue 4, 2013

Carbon–carbon bond construction using boronic acids and aryl methyl sulfides: orthogonal reactivity in Suzuki-type couplings

Author affiliations

Abstract

The Rh(I)-catalysed coupling of aryl and alkenyl boronic acids with simple aryl and alkenyl methyl sulfides is reported. The process employs bench-stable Rh(I) precatalysts incorporating small bite-angle chelating phosphine ligands (R2PCH2PR2, R = iPr, Cy), shows good functional group tolerance, and proceeds under mild reaction conditions. Importantly, aryl bromide activating groups are inert to the reaction conditions, allowing selective reaction at either a methyl sulfide or bromide activating group, depending on catalyst (metal) choice. The scope of the coupling reactions, their combination with Rh-catalysed hydroacylation reactions in cascade processes, together with preliminary mechanistic studies, are all documented.

Graphical abstract: Carbon–carbon bond construction using boronic acids and aryl methyl sulfides: orthogonal reactivity in Suzuki-type couplings

Supplementary files

Article information


Submitted
07 Jan 2013
Accepted
08 Feb 2013
First published
11 Feb 2013

Chem. Sci., 2013,4, 1568-1572
Article type
Edge Article

Carbon–carbon bond construction using boronic acids and aryl methyl sulfides: orthogonal reactivity in Suzuki-type couplings

J. F. Hooper, R. D. Young, I. Pernik, A. S. Weller and M. C. Willis, Chem. Sci., 2013, 4, 1568 DOI: 10.1039/C3SC00052D

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