Mild, Rhodium-Catalyzed Intramolecular Hydroamination of Unactivated Terminal and Internal Alkenes with Primary and Secondary Amines

Zhijian Liu and John F. Hartwig*
Department of Chemistry, University of Illinois Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801
J. Am. Chem. Soc., 2008, 130 (5), pp 1570–1571
DOI: 10.1021/ja710126x
Publication Date (Web): January 10, 2008
Copyright © 2008 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jhartwig@uiuc.edu

Abstract

Abstract Image

We report a series of mild, rhodium-catalyzed hydroaminations of unactivated olefins with primary and secondary alkylamines to form the corresponding five- and six-membered products in excellent yields. The reactions form exclusively the product from hydroamination without competitive oxidative amination or olefin isomerization with catalysts generated from a biaryl dialkyl phosphine and an analogue of Xantphos. A variety of functional groups were tolerated by the hydroamination process, including hydroxyl, halo, cyano, and carboalkoxyl groups.

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History

  • Published In Issue February 06, 2008
  • Received November 7, 2007

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