Nucleophile Promoted Gold Redox Catalysis with diazonium: CBr, C-S and C-P Bond Formation through Catalytic Sandmeyer Coupling

Authors

Haihui Peng, University of South Florida
Rong Cai, West Virginia University
Chang Xu, Ohio University - Main Campus
Hao Chen, Ohio University - Main Campus
Xiaodong Shi, University of South Florida

Document Type

Article

Publication Date

2016

College/Unit

Eberly College of Arts and Sciences

Department/Program/Center

Chemistry

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 to convert Au(I) to Au(III) even without the addition of assisting ligand or photocatalyst. By accelerating 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 selectivity.

Digital Commons Citation

Peng, Haihui; Cai, Rong; Xu, Chang; Chen, Hao; and Shi, Xiaodong, "Nucleophile Promoted Gold Redox Catalysis with diazonium: CBr, C-S and C-P Bond Formation through Catalytic Sandmeyer Coupling" (2016). Faculty & Staff Scholarship. 2364.
https://researchrepository.wvu.edu/faculty_publications/2364

Source Citation

Peng, H., Cai, R., Xu, C., Chen, H., & Shi, X. (2016). Nucleophile promoted gold redox catalysis with diazonium salts: C–Br, C–S and C–P bond formation through catalytic Sandmeyer coupling. Chemical Science, 7(9), 6190–6196. https://doi.org/10.1039/c6sc01742h

Comments

This journal is © The Royal Society of Chemistry 2016