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Issue 1, 2014

Formal anti-Markovnikov hydroamination of terminal olefins

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Abstract

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.

Graphical abstract: Formal anti-Markovnikov hydroamination of terminal olefins

Supplementary files

Article information


Submitted
06 Jul 2013
Accepted
16 Aug 2013
First published
19 Sep 2013

Chem. Sci., 2014,5, 101-106
Article type
Edge Article

Formal anti-Markovnikov hydroamination of terminal olefins

S. M. Bronner and R. H. Grubbs, Chem. Sci., 2014, 5, 101 DOI: 10.1039/C3SC51897C

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