Visible light-mediated gold-catalysed carbon(sp2)–carbon(sp) cross-coupling

Suhong Kim; Jaime Rojas-Martin; F. Dean Toste

doi:10.1039/C5SC03025K

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Visible light-mediated gold-catalysed carbon(sp²)–carbon(sp) cross-coupling†

Suhong Kim,^a Jaime Rojas-Martin^ab and F. Dean Toste*^a

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* Corresponding authors

^a Department of Chemistry, University of California, Berkeley, CA 94720, USA
E-mail: fdtoste@berkeley.edu

^b Departamento de Química Orgánica (Módulo 01), Universidad Autónoma de Madrid, C/Francisco Tomásy Valiente 7, Cantoblanco, 28049 Madrid, Spain

Abstract

A dual photoredox and gold-catalysed cross-coupling reaction of alkynyltrimethylsilanes and aryldiazonium tetrafluoroborates is described. The reaction proceeds through visible-light mediated oxidative addition of aryldiazoniums, transmetalation of alkynyltrimethylsilanes and aryl–alkynyl reductive elimination. Exclusive selectivity for silyl-substituted alkynes is observed, with no reactivity observed for terminal alkynes.

This article is part of the themed collections: ISACS19: Challenges in Organic Chemistry and Top 50 Articles of 2016: Organic Chemistry

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Article information

DOI: https://doi.org/10.1039/C5SC03025K
Article type: Edge Article
Submitted: 14 Mha 2015
Accepted: 26 Nhl 2015
First published: 10 Huk 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2016,7, 85-88

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Visible light-mediated gold-catalysed carbon(sp²)–carbon(sp) cross-coupling

S. Kim, J. Rojas-Martin and F. D. Toste, Chem. Sci., 2016, 7, 85 DOI: 10.1039/C5SC03025K

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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