Electroreduction of unactivated alkenes using water as hydrogen source

Yanwei Wang; Qian Wang; Lei Wu; Kangping Jia; Minyan Wang; Youai Qiu

doi:10.1038/s41467-024-47168-w

Electroreduction of unactivated alkenes using water as hydrogen source

Nat Commun. 2024 Mar 30;15(1):2780. doi: 10.1038/s41467-024-47168-w.

Authors

Yanwei Wang¹, Qian Wang¹, Lei Wu², Kangping Jia¹, Minyan Wang³, Youai Qiu⁴

Affiliations

¹ State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071, China.
² State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, China.
³ State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, China. wangmy@nju.edu.cn.
⁴ State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071, China. qiuyouai@nankai.edu.cn.

Abstract

Herein, we report an electroreduction of unactivated alkyl alkenes enabled by [Fe]-H, which is provided through the combination of anodic iron salts and the silane generated in situ via cathodic reduction, using H₂O as an H-source. The catalytic amounts of Si-additive work as an H-carrier from H₂O to generate a highly active silane species in situ under continuous electrochemical conditions. This approach shows a broad substrate scope and good functional group compatibility. In addition to hydrogenation, the use of D₂O instead of H₂O provides the desired deuterated products in good yields with excellent D-incorporation (up to >99%). Further late-stage hydrogenation of complex molecules and drug derivatives demonstrate potential application in the pharmaceutical industry. Mechanistic studies are performed and provide support for the proposed mechanistic pathway.