Electrochemically enhanced deoxygenative cross-coupling of aryl ketones with heteroarenes through in situ generated benzyl carbocations

Yiyi Zhang; Jianxin Hou; Hui Yang; Shengdong Wang; Kedong Yuan

doi:10.1039/d2ob02065c

Electrochemically enhanced deoxygenative cross-coupling of aryl ketones with heteroarenes through in situ generated benzyl carbocations

Org Biomol Chem. 2022 Dec 21;21(1):80-84. doi: 10.1039/d2ob02065c.

Authors

Yiyi Zhang^{1

2}, Jianxin Hou², Hui Yang², Shengdong Wang¹, Kedong Yuan¹

Affiliations

¹ Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology, the NMPA and State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences and the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou 511436, China. wangshengdong@gzmu.edu.cn.
² Tianjin Key Laboratory of Advanced Functional Porous Materials, Institute for New Energy Materials and Low-Carbon Technologies, School of Materials Science and Engineering, Tianjin University of Technology, Tianjin, 300384, P.R. China.

PMID: 36449338
DOI: 10.1039/d2ob02065c

Abstract

Triflic acids/silanes as cooperative reductants enable the convenient transformation of CO bonds through a multistep reaction pathway in one pot. Electrolysis of the acidic reaction mixture significantly improved carbonyl reduction and thus facilitated the generation of benzyl carbocations, which show high reactivity towards electron-rich heteroarenes for C-C bond formation.

Publication types

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