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Iodine/Manganese Catalyzed Sulfenylation of Indole via Dehydrogenative Oxidative Coupling in Anisole
Author(s) -
Li Weihe,
Wang Hao,
Liu Shengping,
Feng Hua,
Benassi Enrico,
Qian Bo
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000291
Subject(s) - chemistry , anisole , indole test , manganese , catalysis , oxonium ion , combinatorial chemistry , iodine , oxidative phosphorylation , photochemistry , solvent , organic chemistry , ion , biochemistry
This protocol describes an iodine/manganese catalytic system for dehydrogenative oxidative coupling reaction of indoles with thiols in anisole. Particularly, the dual roles of anisole have been first demonstrated as a solvent and as a promoter via the formation of an oxonium ion intermediate to accelerate the generation of products. A series of sulfenylindoles are readily constructed under aerobic mild reaction conditions. In addition, the achievement for preparing anticancer and anti‐AIDS drugs testifies the practicability of this approach. The mechanism studies disclose probable alternative pathways and a single‐electron transfer process are involved in this transformation.