Transition-Metal-Free, Reductive Csp2-Csp3 Bond Constructions via Electrochemically Induced Alkyl Radicals

Shuhua Wu; Jiahui Huang; Lulu Kang; Yiyi Zhang; Kedong Yuan

doi:10.1021/acs.orglett.3c04307

Transition-Metal-Free, Reductive Csp²-Csp³ Bond Constructions via Electrochemically Induced Alkyl Radicals

Org Lett. 2024 Jan 26;26(3):763-768. doi: 10.1021/acs.orglett.3c04307. Epub 2024 Jan 16.

Authors

Shuhua Wu^{1

2}, Jiahui Huang¹, Lulu Kang^{1

2}, Yiyi Zhang^{1

2}, 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.
² Tianjin Key Laboratory of Advanced Functional Porous Materials, Institute for New Energy Materials & Low-Carbon Technologies, School of Materials Science and Engineering, Tianjin University of Technology, Tianjin 300384, P. R. China.

PMID: 38227333
DOI: 10.1021/acs.orglett.3c04307

Abstract

Construction of the Csp²-Csp³ bond without the aid of transition metal catalysts has been achieved by coupling the electrogenerated alkyl radicals with electron deficient (hetero)arenes in an undivided cell. Simultaneous cathodic reduction of both unactivated alkyl halides and cyanobenzenes under high potential enables radical-radical cross-coupling to deliver alkylarenes in the absence of transition metals. Depending on the coupling partner, the electrogenerated alkyl radicals can also proceed the Minisci-type reaction with N-heteroarenes without redox agents.