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Photoredox‐Catalyzed Functionalization of Alkenes with Thiourea Dioxide: Construction of Alkyl Sulfones or Sulfonamides
Author(s) -
Li Yuewen,
Liu JinBiao,
He FuSheng,
Wu Jie
Publication year - 2020
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201900505
Subject(s) - chemistry , photoredox catalysis , regioselectivity , surface modification , alkyl , electrophile , thiourea , sulfur dioxide , photochemistry , catalysis , quenching (fluorescence) , organic chemistry , combinatorial chemistry , fluorescence , photocatalysis , physics , quantum mechanics
Summary of main observation and conclusion Sulfonylation of alkenes through photoredox‐catalyzed functionalization of alkenes with thiourea dioxide under visible‐light irradiation is achieved. The reaction of alkenes, thiourea dioxide and electrophiles provides a green and efficient access to alkyl sulfones and sulfonamides. A broad reaction scope is presented with good functional group compatibility and excellent regioselectivity. A plausible mechanism involving a radical addition process with sulfur dioxide radical anion (SO 2 ‐ ) derived from the oxidation of sulfur dioxide anion (SO 2 2– ) is proposed, which is supported by fluorescence quenching experiments.