A novel fluorous-tagged ammonia surrogate has been synthesized and its application to the synthesis of anilines by Buchwald-Hartwig palladium-catalyzed amidation-hydrolysis protocol is described. Primary anilines were obtained in moderate to good yields after a sequence of two reaction steps involving fluorous separation techniques for their purification. Preliminary results indicate that N-substituted anilines can also be obtained using just N-substituted-FBoc carbamates as the nitrogen source.
Johnson and Johnson Pharmaceutical Research and Development, Research and Early Development Europe, CNS-Psychiatry, Division of Janssen-Cilag, Medicinal Chemistry Department, Jarama 75, 45007 Toledo, Spain. atrabanc@prdes.jnj.com