Nucleophile Promoted Gold Redox Catalysis with Diazonium Salts: C-Br, 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, Edison Biotechnology Institute
Hao Chen, Edison Biotechnology Institute
Xiaodong Shi, University of South FloridaFollow

Document Type

Article

Publication Date

2016

Digital Object Identifier (DOI)

https://doi.org/10.1039/C6SC01742H

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.

Rights Information

This work is licensed under a Creative Commons Attribution 3.0 License.

Was this content written or created while at USF?

Yes

Citation / Publisher Attribution

Chemical Science, v. 7, issue 9, p. 6190-6196

Scholar Commons Citation

Peng, Haihui; Cai, Rong; Xu, Chang; Chen, Hao; and Shi, Xiaodong, "Nucleophile Promoted Gold Redox Catalysis with Diazonium Salts: C-Br, C-S and C-P Bond Formation through Catalytic Sandmeyer Coupling" (2016). Chemistry Faculty Publications. 31.
https://digitalcommons.usf.edu/chm_facpub/31