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Synthesis of Cyclic Guanidines via Pd-Catalyzed Alkene Carboamination

Blane P. Zavesky, Nicholas R. Babij, Jonathan A. Fritz and John P. Wolfe*

*Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, United States, Email: jpwolfeumich.edu

B. P. Zavesky, N. R. Babij, J. A. Fritz, J. P. Wolfe, Org. Lett., 2013, 15, 5420-5423.

DOI: 10.1021/ol402377y (free Supporting Information)


Abstract

Palladium-catalyzed alkene carboamination reactions between acyclic N-allyl guanidines and aryl or alkenyl halides provide substituted 5-membered cyclic guanidines in good yield. This method allows access to a number of different cyclic guanidine derivatives in only two steps from readily available allylic amines.

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Key Words

N-heterocycles, Guanidines


ID: J54-Y2013