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Visible Light‐Induced Iodine‐Catalyzed Transformation of Terminal Alkynes to Primary Amides via CC Bond Cleavage under Aqueous Conditions
Author(s) -
Dighe Shashikant U.,
Batra Sanjay
Publication year - 2016
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.201500906
Subject(s) - chemistry , hydroamination , catalysis , bond cleavage , aqueous solution , photochemistry , acetylene , visible spectrum , diiodomethane , iodine , ammonia , cleavage (geology) , triple bond , polymer chemistry , medicinal chemistry , organic chemistry , double bond , physics , geotechnical engineering , optoelectronics , surface energy , fracture (geology) , engineering
The visible light‐induced iodine‐catalyzed oxidative cleavage of the CC bond for transforming terminal alkynes into primary amides in the presence of ammonia under aqueous conditions is described. This metal‐free protocol which ensued via initial hydroamination of the acetylene bond followed by liberation of diiodomethane (CH 2 I 2 ) was found to be applicable to aromatic, heteroaromatic and aliphatic alkynes.