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Intramolecular Pd(II)-Catalyzed Aerobic Oxidative Amination of Alkenes: Synthesis of Six-Membered N-Heterocycles

Zhan Lu and Shannon S. Stahl*

*Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States, Email: stahlchem.wisc.edu

Z. Lu, S. S. Stahl, Org. Lett., 2012, 14, 1234-1237.

DOI: 10.1021/ol300030w (free Supporting Information)


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Abstract

Use of a base-free Pd(DMSO)2(TFA)2 catalyst enables the synthesis of six-membered nitrogen heterocycles via a Wacker-type aerobic oxidative cyclization of alkenes. Various heterocycles, including morpholines, piperidines, piperazines and piperazinones, are accessible by this method.


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Enantioselective Pd(II)-Catalyzed Aerobic Oxidative Amidation of Alkenes and Insights into the Role of Electronic Asymmetry in Pyridine-Oxazoline Ligands

R. I. McDonald, P. W. White, A. B. Weinstein, C. P. Tam, S. S. Stahl, Org. Lett., 2011, 13, 2830-2833.


Key Words

Morpholines, Piperidines, Piperazines, Wacker-Tsuji Oxidation, Oxygen


ID: J54-Y2012-0550