4.8 Article

Mild, rhodium-catalyzed intramolecular hydroamination of unactivated terminal and internal Alkenes with primary and secondary amines

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 5, Pages 1570-+

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja710126x

Keywords

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Funding

  1. NIGMS NIH HHS [GM-55382, R29 GM055382, R37 GM055382, R01 GM055382-14, R01 GM055382] Funding Source: Medline

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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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