One-Pot Tandem Photoredox and Cross-Coupling Catalysis with a Single Palladium Carbodicarbene Complex

Yu-Cheng Hsu; Vincent C-C Wang; Ka-Chun Au-Yeung; Chung-Yu Tsai; Chun-Chi Chang; Bo-Chao Lin; Yi-Tsu Chan; Chao-Ping Hsu; Glenn P A Yap; Titel Jurca; Tiow-Gan Ong

doi:10.1002/anie.201800951

One-Pot Tandem Photoredox and Cross-Coupling Catalysis with a Single Palladium Carbodicarbene Complex

Angew Chem Int Ed Engl. 2018 Apr 16;57(17):4622-4626. doi: 10.1002/anie.201800951. Epub 2018 Mar 13.

Authors

Yu-Cheng Hsu^{1

2}, Vincent C-C Wang^{1

3}, Ka-Chun Au-Yeung¹, Chung-Yu Tsai¹, Chun-Chi Chang¹, Bo-Chao Lin¹, Yi-Tsu Chan², Chao-Ping Hsu¹, Glenn P A Yap⁴, Titel Jurca⁵, Tiow-Gan Ong^{1

6}

Affiliations

¹ Institute of Chemistry, Academia Sinica, Taipei, 11529, Taiwan, Republic of China.
² Department of Chemistry, National Taiwan University, Taipei, 10161, Taiwan, Republic of China.
³ Department of Chemistry, Ångström Laboratory, Uppsala University, Uppsala, 75120, Sweden.
⁴ Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware, 19716, USA.
⁵ Department of Chemistry & Cluster for the Rational Design of Catalysts for Energy Applications and Propulsion, University of Central Florida, Orlando, Florida, 32816, USA.
⁶ Department of Applied Chemistry, National Chiao Tung University, Hsinchu, 300, Taiwan, Republic of China.

PMID: 29461658
DOI: 10.1002/anie.201800951

Abstract

The combination of conventional transition-metal-catalyzed coupling (2 e^- process) and photoredox catalysis (1 e^- process) has emerged as a powerful approach to catalyze difficult cross-coupling reactions under mild reaction conditions. Reported is a palladium carbodicarbene (CDC) complex that mediates both a Suzuki-Miyaura coupling and photoredox catalysis for C-N bond formation upon visible-light irradiation. These two catalytic pathways can be combined to promote both conventional transition-metal-catalyzed coupling and photoredox catalysis to mediate C-H arylation under ambient conditions with a single catalyst in an efficient one-pot process.

Keywords: carbenes; cross-coupling; palladium; photocatalysis; reaction mechanisms.

Publication types

Research Support, Non-U.S. Gov't