Facilitating Gold Redox Catalysis with Electrochemistry: An Efficient Chemical-Oxidant-Free Approach

Authors

Xiaohan Ye, University of South Florida, Tampa
Pengyi Zhao, New Jersey Institute of Technology
Shuyao Zhang, University of South Florida, Tampa
Yanbin Zhang, Fudan University
Qilin Wang, University of South Florida, Tampa
Chuan Shan, University of South Florida, Tampa
Lukasz Wojtas, University of South Florida, Tampa
Hao Guo, Fudan University
Hao Chen, New Jersey Institute of Technology
Xiaodong Shi, University of South Florida, Tampa

Document Type

Article

Publication Date

11-25-2019

Abstract

Due to the high oxidation potential between Au^I and Au^III, gold redox catalysis requires at least stoichiometric amounts of a strong oxidant. We herein report the first example of an electrochemical approach in promoting gold-catalyzed oxidative coupling of terminal alkynes. Oxidation of Au^I to Au^III was successfully achieved through anode oxidation, which enabled facile access to either symmetrical or unsymmetrical conjugated diynes through homo-coupling or cross-coupling. This report extends the reaction scope of this transformation to substrates that are not compatible with strong chemical oxidants and potentiates the versatility of gold redox chemistry through the utilization of electrochemical oxidative conditions.

Identifier

85072190050 (Scopus)

Publication Title

Angewandte Chemie International Edition

External Full Text Location

https://doi.org/10.1002/anie.201909082

e-ISSN

15213773

ISSN

14337851

PubMed ID

31407454

First Page

17226

Last Page

17230

Issue

48

Volume

58

Grant

CHE-1665122

Fund Ref

National Science Foundation

Recommended Citation

Ye, Xiaohan; Zhao, Pengyi; Zhang, Shuyao; Zhang, Yanbin; Wang, Qilin; Shan, Chuan; Wojtas, Lukasz; Guo, Hao; Chen, Hao; and Shi, Xiaodong, "Facilitating Gold Redox Catalysis with Electrochemistry: An Efficient Chemical-Oxidant-Free Approach" (2019). Faculty Publications. 7185.
https://digitalcommons.njit.edu/fac_pubs/7185