Metal-free difunctionalization of alkynes to access tetrasubstituted olefins through spontaneous selenosulfonylation of vinylidene ortho-quinone methide (VQM). Issue 5 (11th January 2019)

• Record Type: Journal Article
• Authors: Huang, Shengli; Chen, Zhili; Mao, Hui; Hu, Fangli; Li, Dongmei; Tan, Yu; Yang, Fengqing; Qin, Wenling
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 5(2019)
• Page Start: 1121
• Page End: 1129
• Publication Date: 2019-01-11
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob02967a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A metal-free protocol for difunctionalization of alkynes through spontaneous selenosulfonylation of vinylidene ortho -quinone methide (VQM) was developed with good yields and excellent stereoselectivities. Abstract : A metal-free difunctionalization of alkynes to access tetrasubstituted olefins through spontaneous selenosulfonylation of vinylidene ortho -quinone methide (VQM) was described herein. The reaction was conducted under mild conditions without any catalysts or additives. Preliminary mechanism studies revealed that the formation of VQM was the key for this alkyne di-functionalization reaction. The reaction could be applied in the enantioselective asymmetric synthesis of axially chiral styrene. Furthermore, the selenosulfonylation adducts can be transformed into useful naphtho[2, 1- b ]furan and benzofuran scaffolds.