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Intermolecular Hydroamination of 1,3-Dienes Catalyzed by Bis(phosphine)carbodicarbene-Rhodium Complexes

Matthew J. Goldfogel, Courtney C. Roberts and Simon J. Meek*

*Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States, Email: sjmeekunc.edu

M. J. Goldfogel, C. C. Roberts, S. J. Meek, J. Am. Chem. Soc., 2014, 136, 6227-6230.

DOI: 10.1021/ja502275w (free Supporting Information)


Abstract

The use of a carbodicarbene-based pincer ligand scaffold enables a site-selective Rh(I)-catalyzed intermolecular hydroamination of 1,3-dienes with aryl and alkyl amines. Transformations proceed in the presence of 1.0-5.0 mol % Rh complex at 35 - 120 C; allylic amines are obtained in up to 97% yield and with >98:2 site selectivity.

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Key Words

allylic amines


ID: J48-Y2014