Dithiocyanation of Alkynes with N‐Thiocyanato‐dibenzenesulfonimide and Ammonium Thiocyanate. Issue 20 (24th May 2022)

• Record Type: Journal Article
• Authors: Duan, Yongjie; Liang, Kun; Yin, Hongquan; Chen, Fu‐Xue
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 20(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-05-24
• Subjects: Alkenes -- Alkynes -- Difunctionalization -- Electrophilic Addition -- Thiocyanates; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202200359
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Organic thiocyanates widely exist in natural products, and act as important precursors for organic synthesis. An efficient dithiocyanation of alkynes with N ‐thiocyanato‐dibenzenesulfonimide (NTSI) as the SCN + cation and ammonium thiocyanate as the SCN ‐ anion sources has been developed. Highly active electrophilic reagent NTSI could react with various types of alkynes to build C(sp 2 )−SCN bond to provide a variety of dithiocyanato olefin compounds under simple and mild conditions. Trace amount of water is beneficial to the dissociation of ammonium thiocyanate, which makes the SCN ‐ anion easier to participate in the reaction. The protocol owns a broad substrates scope including terminal and internal, alkyl and aryl alkynes, excellent functional group tolerance and good regioselectivity. Abstract : A new electrophilic/nucleophilic dithiocyanation of alkynes with N ‐thiocyanato‐dibenzenesulfonimide (NTSI) and NH4 SCN has been demonstrated. The protocol features a broad substrate scope, mild reaction condition, and high yields.