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Sustainable and Site‐Selective C−H Sulfenylation of Aromatic Compounds with Thiol using Catalytic Graphene Oxide and NaI
Author(s) -
Choudhury Prasun,
Roy Babli,
Basu Basudeb
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700275
Subject(s) - chemistry , oxidizing agent , catalysis , resorcinol , reagent , oxide , thiol , graphene , sulfur , combinatorial chemistry , reducing agent , metal , indole test , synthon , organic chemistry , nanotechnology , materials science
Graphene oxide (GO) in combination with NaI is used as the catalytic system for site‐selective C−H sulfenylation of 1 H ‐indole, 2‐naphthol, resorcinol and 2‐naphthylamines with thiols. The reaction is usually achieved in the presence of metal catalysts as well as under metal‐free conditions using iodine and a strong oxidizing agent. The present protocol avoids the use of any metal catalysts, strong oxidizing agents and the use of thiols instead of other sulfur‐based reagents making it atom‐economic and environmentally benign. Broader tolerance to functional groups has been tested and a plausible mechanism is proposed. The recovered GO can be recycled without significant loss in catalytic activity up to four runs.