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Published September 19, 2013 | Supplemental Material + Published
Journal Article Open

Formal anti-Markovnikov hydroamination of terminal olefins


A new strategy to access linear amines from terminal olefin precursors is reported. This two-step, one-pot hydroamination methodology employs sequential oxidation and reduction catalytic cycles. The formal hydroamination transformation proceeds with excellent regioselectivity, and only the anti-Markovnikov product is observed. Up to 70% yield can be obtained from styrenes or aliphatic olefins and either primary or secondary aromatic amines. Additionally, the scope is broad with respect to the olefin and accommodates a variety of functionalities; we demonstrate that amines with removable aryl protecting groups may be utilized to allow access to a more diverse array of hydroamination adducts.

Additional Information

© 2014 The Royal Society of Chemistry. Received 06 Jul 2013, Accepted 16 Aug 2013; First published online 19 Sep 2013. Research reported in this publication was supported by the National Institute of General Medical Sciences of the National Institutes of Health under Award Number F32GM102984. NMR spectra were obtained by instruments supported by the NIH (RR027690). We are grateful to J. S. Cannon, B. Morandi, and Z. K. Wickens for helpful discussions.

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Published - c3sc51897c.pdf

Supplemental Material - c3sc51897c_si.pdf


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Additional details

August 19, 2023
October 25, 2023