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

Haihui Peng, Rong Cai, Chang Xu, Hao Chen, Xiaodong Shi

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)6190-6196
Number of pages7
JournalChemical Science
Volume7
Issue number9
DOIs
StatePublished - 2016
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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