Electrochemical Direct Thiolation of Lactams with Mercaptans: An Efficient Access to N‐Acylsulfenamides. Issue 33 (2nd September 2021)

• Record Type: Journal Article
• Authors: Wei, Zhaoxin; Wang, Renjie; Zhang, Yonghong; Wang, Bin; Xia, Yu; Abdukader, Ablimit; Xue, Fei; Jin, Weiwei; Liu, Chenjiang
• Is Part Of: European journal of organic chemistry. Issue 33(2021)
• Page Start: 4728
• Page End: 4732
• Publication Date: 2021-09-02
• Subjects: Lactams -- Mercaptans -- N-acylsulfenamides -- N−S bonds -- Thiolation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202100924
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: An efficient and eco‐friendly electrochemical methodology for the oxidative cross coupling hydrogen evolution (CCHE) reactions of lactams with thiols is presented. Various electron deficient N ‐acylsulfenamides are smoothly produced in modest to excellent yields without using any external oxidant. Elementary mechanistic insight supports a possible free radical process and hydrogen is the only side product. This approach provides a safe, convenient, and economical preparation of synthetically important N ‐thiophthalimides on a gram scale. Abstract : A variety of N ‐acylsulfenamides are produced by the electrochemically enabled cross‐coupling of readily available feedstocks under standard conditions. This protocol is practical and has wide substrate scope with good reaction efficiency (38 examples, up to 97 % yield). A possible free radical mechanism is preliminarily demonstrated.