Electrochemically selective double C(sp2)–X (X = S/Se, N) bond formation of isocyanides. Issue 42 (12th October 2021)

• Record Type: Journal Article
• Authors: Guan, Zhipeng; Zhu, Shuxiang; Yang, Yankai; Liu, Yanlong; Wang, Siyuan; Bu, Faxiang; Cong, Hengjiang; Alhumade, Hesham; Zhang, Heng; Lei, Aiwen
• Is Part Of: Chemical science. Volume 12:Issue 42(2021)
• Page Start: 14121
• Page End: 14125
• Publication Date: 2021-10-12
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1sc04475c
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : We have developed an efficient and sustainable electrochemical strategy for the double C(sp 2 )–X (S/Se, N) bond formation of isocyanides simultaneously. A series of novel isothio/selenoureas were obtained via a three-component cross-coupling. Abstract : The construction of C(sp 2 )–X (X = B, N, O, Si, P, S, Se, etc .) bonds has drawn growing attention since heteroatomic compounds play a prominent role from biological to pharmaceutical sciences. The current study demonstrates the C(sp 2 )–S/Se and C(sp 2 )–N bond formation of one carbon of isocyanides with thiophenols or disulfides or diselenides and azazoles simultaneously. The reported findings could provide access to novel multiple isothioureas, especially hitherto rarely reported selenoureas. The protocol showed good atom-economy and step-economy with only hydrogen evolution and theoretical calculations accounted for the stereoselectivity of the products. Importantly, the electrochemical reaction could exclusively occur at the isocyano part regardless of the presence of susceptible radical acceptors, such as a broad range of arenes and alkynyl moieties, even alkenyl moieties.