127686-13-9Relevant academic research and scientific papers
Facile and Effective Synthesis of Unusually Substituted Aromatic N-Phenylamides
Kobs, Uwe,Neumann, Wilhelm P.
, p. 2191 - 2194 (2007/10/02)
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 trialkylstannyl-substituted aromatic, heterocyclic or vinylic hydrocarbons with aryl isocyanates in the presence of aluminium trichloride provides the corresponding N-aryl-substituted amides 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 ipso substitution, to obtain isomer patterns not accessible by normal electrophilic substitution reactions, e. g. substitution in meta position with respect to a methoxy group.
