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Issue 9, 2016
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Nucleophile promoted gold redox catalysis with diazonium salts: C–Br, C–S and C–P bond formation through catalytic Sandmeyer coupling

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Abstract

Gold-catalyzed C-heteroatom (C–X) coupling reactions are evaluated without using sacrificial oxidants. Vital to the success of this methodology is the nucleophile-assisted activation of aryldiazonium salts, which could be an effective oxidant for converting Au(I) to Au(III) even without the addition of an assisting ligand or photocatalyst. By accelerating the reaction kinetics to outcompete C–C homo-coupling or diazonium dediazoniation, gold-catalyzed Sandmeyer reactions were achieved with different nucleophiles, forming C–Br, C–S and C–P bonds in high yields and selectivities.

Graphical abstract: Nucleophile promoted gold redox catalysis with diazonium salts: C–Br, C–S and C–P bond formation through catalytic Sandmeyer coupling

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Publication details

The article was received on 20 Apr 2016, accepted on 09 Jun 2016 and first published on 10 Jun 2016


Article type: Edge Article
DOI: 10.1039/C6SC01742H
Citation: Chem. Sci., 2016,7, 6190-6196
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    Nucleophile promoted gold redox catalysis with diazonium salts: C–Br, C–S and C–P bond formation through catalytic Sandmeyer coupling

    H. Peng, R. Cai, C. Xu, H. Chen and X. Shi, Chem. Sci., 2016, 7, 6190
    DOI: 10.1039/C6SC01742H

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