A Caltech Library Service

Formal anti-Markovnikov hydroamination of terminal olefins

Bronner, Sarah M. and Grubbs, Robert H. (2013) Formal anti-Markovnikov hydroamination of terminal olefins. Chemical Science, 5 (1). pp. 101-106. ISSN 2041-6520. PMCID PMC3855355. doi:10.1039/c3sc51897c.

PDF - Published Version
See Usage Policy.

PDF - Supplemental Material
See Usage Policy.


Use this Persistent URL to link to this item:


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.

Item Type:Article
Related URLs:
URLURL TypeDescription CentralArticle
Grubbs, Robert H.0000-0002-0057-7817
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.
Funding AgencyGrant Number
NIH Postdoctoral FellowshipF32GM102984
Issue or Number:1
PubMed Central ID:PMC3855355
Record Number:CaltechAUTHORS:20140110-111514418
Persistent URL:
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:43311
Deposited By: Tony Diaz
Deposited On:10 Jan 2014 20:53
Last Modified:10 Nov 2021 16:36

Repository Staff Only: item control page