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C−H Mono‐Nitration of Indolines using tert ‐Butyl Nitrite
Author(s) -
Sau Sudip,
Bose Anima,
Mal Prasenjit
Publication year - 2019
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.201900464
Subject(s) - nitration , chemistry , regioselectivity , nitrite , acetonitrile , electrophilic aromatic substitution , organic chemistry , amyl nitrite , medicinal chemistry , nitrate , catalysis , medicine , anesthesia
Nitration reactions on non‐prefunctionalized aromatic or heteroaromatic compounds are generally done under harsh conditions. However, these reactions are non‐selective to mono‐substitution and often produce a mixture of products. Herein we report a mild mono‐nitration reaction on indolines, either at −C 5 or −C 7 positions, with 100% regioselectivity using tert ‐butyl nitrite. The reactions are carried out in acetonitrile and without any additives except nitrating agent tert ‐butyl nitrite.