ISSN:
0009-2940
Keywords:
Electrophilic aromatic substitution
;
Carbo-destannylation
;
Amides, synthesis of
;
Trialkylarylstannanes, application of
;
Aryl isocyanates
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19901231117
