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Lewis‐Acid‐Catalyzed Direct Nucleophilic Substitution Reaction of Alcohols for the Functionalization of Aromatic Amines
Author(s) -
Nayal Onkar S.,
Thakur Maheshwar S.,
Rana Rohit,
Upadhyay Rahul,
Maurya Sushil K.
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201803530
Subject(s) - chemistry , enamine , alkylation , imine , catalysis , lewis acids and bases , nucleophile , surface modification , nucleophilic substitution , organic chemistry , combinatorial chemistry , substitution reaction , nucleophilic aromatic substitution
N‐Alkylation of aromatic amines with alcohols is an efficient route for the synthesis of higher benzylamines. Herein, we explore an efficient catalytic activity of tin(ii) triflate for the N‐alkylation of secondary anilines with alcohols for the synthesis of tertiary benzylamines. Mechanistic studies suggest that the developed protocol follows direct nucleophilic substitution pathway instead of imine or enamine pathway. The developed method is also useful for the synthesis of secondary amines as well as late stage functionalization of naturally occurring alcohols.