Mild, rhodium-catalyzed intramolecular hydroamination of unactivated terminal and internal alkenes with primary and secondary amines.
作者信息
Liu Zhijian, Hartwig John F
机构信息
Department of Chemistry, University of Illinois Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, USA.
出版信息
J Am Chem Soc. 2008 Feb 6;130(5):1570-1. doi: 10.1021/ja710126x. Epub 2008 Jan 10.
Abstract
摘要
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3
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