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Visible-light photoredox-catalyzed dual C–C bond cleavage: synthesis of 2-cyanoalkylsulfonylated 3,4-dihydronaphthalenes through the insertion of sulfur dioxide

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Abstract

An efficient novel visible-light photoredox-catalyzed dual carbon–carbon bond cleavage of methylenecyclopropanes and cycloketone oximes for the synthesis of 2-cyanoalkylsulfonated 3,4-dihydronaphthalenes through the insertion of sulfur dioxide is established. This dual cleavage of carbon–carbon bonds involves a radical pathway and goes through a sequence of iminyl radical formation, carbon–carbon bond cleavage, sulfur dioxide insertion, sulfonyl radical addition, another carbon–carbon bond cleavage, and intramolecular cyclization.

Graphical abstract: Visible-light photoredox-catalyzed dual C–C bond cleavage: synthesis of 2-cyanoalkylsulfonylated 3,4-dihydronaphthalenes through the insertion of sulfur dioxide

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Article information


Submitted
30 Dec 2019
Accepted
22 Jan 2020
First published
23 Jan 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Visible-light photoredox-catalyzed dual C–C bond cleavage: synthesis of 2-cyanoalkylsulfonylated 3,4-dihydronaphthalenes through the insertion of sulfur dioxide

Y. Liu, Q. Wang, Z. Chen, H. Li, B. Xiong, P. Zhang and K. Tang, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC10057A

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