Electrochemical Synthesis of α-Thiocyanated/Methoxylated Ketones Using Enol Acetates

Peng Zhang; Junwei Ma; Xuan Liu; Fei Xue; Yonghong Zhang; Bin Wang; Weiwei Jin; Yu Xia; Chenjiang Liu

doi:10.1021/acs.joc.3c01417

Electrochemical Synthesis of α-Thiocyanated/Methoxylated Ketones Using Enol Acetates

J Org Chem. 2023 Dec 1;88(23):16122-16131. doi: 10.1021/acs.joc.3c01417. Epub 2023 Nov 14.

Authors

Peng Zhang¹, Junwei Ma², Xuan Liu¹, Fei Xue¹, Yonghong Zhang¹, Bin Wang¹, Weiwei Jin¹, Yu Xia¹, Chenjiang Liu^{1

3}

Affiliations

¹ Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi 830017, P. R. China.
² Key Laboratory of Optic-Electric Sensing and Analytical Chemistry for Life Sciences, MOE, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China.
³ College of Future Technology, Xinjiang University, Urumqi 830017, P. R. China.

PMID: 37963225
DOI: 10.1021/acs.joc.3c01417

Abstract

We have developed the synthesis of α-substituted ketone compounds with enol acetates in an electrochemical way. By using cheap NH₄SCN and MeOH as the radical sources, a series of valuable α-thiocyanates/methoxy ketones were synthesized under mild electrolysis conditions in acceptable yields with diverse functional group compatibility. Additionally, the scale-up experiment and synthetic transformations reveal potential applications in organic synthesis.