Room-temperature ortho-alkoxylation and -halogenation of N-tosylbenzamides by using palladium(II)-catalyzed C-H activation.
The N-tosylcarboxamide group can direct the room-temperature palladium-catalyzed C-H alkoxylation and halogenation of substituted arenes in a simple and mild procedure. The room-temperature stoichiometric cyclopalladation of N-tosylbenzamide was first studied, and the ability of the palladacycle to react with oxidants to form C-X and C-O bonds under mild conditions was demonstrated. The reaction conditions were then adapted to promote room-temperature ortho-alkoxylations and ortho-halogenations of N-tosylbenzamides using palladium as catalyst. The scope and limitation of both alkoxylations and halogenations was studied and the subsequent functional transformation of the N-tosylcarboxamide group through nucleophilic additions was evaluated. This methodology offers a simple and mild route to diversely functionalized arenes.
Normandie Université (France); Université de Caen Basse-Normandie, CERMN (EA 4258 - FR CNRS 3038 INC3M, - SF 4206 ICORE) UFR des Sciences Pharmaceutiques, Bd Becquerel, CS 14032 Caen cedex 5 (France), Fax: (+33) 231566803.
Florent
F
Péron
Christine
C
Fossey
Jana
J
Sopkova-de Oliveira Santos
Thomas
T
Cailly
Frédéric
F
Fabis
D002384:Catalysis; D054879:Halogenation; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D010165:Palladium
CH activation; alkoxylation; halogenation; palladium; synthetic methods