(Z)-Tetrahydrothiophene and (Z)-tetrahydrothiopyran synthesis through nucleophilic substitution and intramolecular cycloaddition of alkynyl halides and EtOCS2K. Issue 31 (25th July 2019)

• Record Type: Journal Article
• Authors: Luo, Xianglin; Li, Yibiao; Chen, Xiuwen; Song, Zhiyan; Liang, Junyi; Liao, Chunshu; Zhu, Zhongzhi; Chen, Lu
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 31(2019)
• Page Start: 7315
• Page End: 7319
• Publication Date: 2019-07-25
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob01370a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : This protocol provides a novel method for the synthesis of ( Z )-tetrahydrothiophene derivatives through the formation of C–S bonds under transition-metal-free condition using thiyl radical intramolecular cycloaddition cascade strategy. Abstract : This protocol provides a novel, environmentally friendly and simple method for the synthesis of ( Z )-tetrahydrothiophene derivatives using the nucleophilic thiyl radical intramolecular cycloaddition cascade process to construct C–S bonds under transition-metal-free conditions. This transformation process offers a broad substrate scope, good functional group tolerance, and excellent stereoselectivity ( Z / E ratios up to 99/1). Moreover, the process uses odourless, stable and cheap EtOCS2 K as the sulfur source.