Synthesis of Dihydrothiophenes and Thiophenes by the Strategic Use of 2‐Vinylidene‐1, 3‐dithiolane as a Masked Thiolate Anion. Issue 5 (9th January 2014)

• Record Type: Journal Article
• Authors: Fang, Zhongxue; Liao, Peiqiu; Yang, Zonglian; Wang, Yeming; Zhou, Biying; Yang, Yang; Bi, Xihe
• Is Part Of: European journal of organic chemistry. Issue 5(2014)
• Page Start: 924
• Page End: 927
• Publication Date: 2014-01-09
• Subjects: Sulfur heterocycles -- Annulation -- Ketenes -- Dithioacetals -- Fragmentation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201301624
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Differently substituted 4‐(1, 3‐dithiolan‐2‐ylidene)but‐1‐ynes were conveniently converted into the corresponding thiophenes and dihydrothiophenes in good to high yields under mild conditions. 1, 3‐Dithiolan‐2‐ylidene acted as a masked thiolate anion and underwent tandem fragmentation and 5‐ exo ‐ dig annulation with an alkyne moiety to form the five‐membered sulfur heterocycles. Abstract : An efficient and atom‐economic approach for the preparation of densely functionalized 2, 3‐dihydrothiophenes and thiophenes is reported. For the first time, the strategic use of 1, 3‐dithiolan‐2‐ylidene as a masked thiolate anion is used in a tandem fragmentation and 5‐ exo ‐ dig annulation with an alkyne moiety to form five‐membered sulfur heterocycles.