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

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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.

Graphical abstract: Metal-free difunctionalization of alkynes to access tetrasubstituted olefins through spontaneous selenosulfonylation of vinylidene ortho-quinone methide (VQM)

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Publication details

The article was received on 28 Nov 2018, accepted on 07 Jan 2019 and first published on 07 Jan 2019


Article type: Paper
DOI: 10.1039/C8OB02967A
Org. Biomol. Chem., 2019,17, 1121-1129

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    Metal-free difunctionalization of alkynes to access tetrasubstituted olefins through spontaneous selenosulfonylation of vinylidene ortho-quinone methide (VQM)

    S. Huang, Z. Chen, H. Mao, F. Hu, D. Li, Y. Tan, F. Yang and W. Qin, Org. Biomol. Chem., 2019, 17, 1121
    DOI: 10.1039/C8OB02967A

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