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Allylic Aminations with Hindered Secondary Amine Nucleophiles Catalyzed by Heterobimetallic Pd-Ti Complexes

Whitney K. Walker, Diana L. Anderson, Ryjul W. Stokes, Stacey J. Smith and David J. Michaelis*

*Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, United States, Email: dmichaelischem.byu.edu

W. K. Walker, D. L. Anderson, R. W. Stokes, S. J. Smith, D. J. Michaelis, Org. Lett., 2015, 17, 752-755.

DOI: 10.1021/acs.orglett.5b00058 (free Supporting Information)



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Abstract

Phosphinoamide-scaffolded heterobimetallic palladium-titanium complexes are highly effective catalysts for allylic aminations of allylic chlorides with hindered secondary amine nucleophiles. Various sterically bulky secondary amines are efficiently allylated in high yields with low catalyst loadings. Piperidine and pyrrolidine products are also efficiently generated via intramolecular aminations.

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Key Words

allylic amines, Tsuji-Trost Reaction


ID: J54-Y2015