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Tin for organic synthesis, 3. Facile and effective synthesis of unusually substituted aromatic N ‐phenylamides
Author(s) -
Kobs Uwe,
Neumann Wilhelm P.
Publication year - 1990
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19901231117
Subject(s) - chemistry , tin , aryl , electrophilic aromatic substitution , electrophilic substitution , electrophile , medicinal chemistry , group (periodic table) , leaving group , organic chemistry , combinatorial chemistry , stereochemistry , catalysis , alkyl
A mild and effective new method for the preparation of a variety of arylamides 3a‐i as well as heterocyclic 5a,b and 6 and olefinic amides 7, 9 is described. The reaction of tri‐alkylstannyl‐substituted aromatic, heterocyclic or vinylic hy‐drocarbons with aryl isocyanates in the presence of aluminium trichloride provides the corresponding N‐aryl‐substituted am‐ides in good to excellent yields. The stannyl group serves as a powerful leaving group superior to hydrogen by several powers of ten which allows, via ips0 substitution, to obtain isomer patterns not accessible by normal electrophilic substi‐ tution reactions, e. g. substitution in meta position with respect to a methoxy group.