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Issue 1, 2018
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Site-selective bromination of sp3 C–H bonds

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Abstract

A method for converting sp3 C–H to C–Br bonds using an N-methyl sulfamate directing group is described. The reaction employs Rh2(oct)4 and a mixture of NaBr and NaOCl and is performed in aqueous solution open to air. For all sulfamates examined, oxidation occurs with high selectivity at the γ-carbon, affording a uniquely predictable method for C–H bond halogenation. Results from a series of mechanistic experiments suggest that substrate oxidation likely proceeds by a radical chain process. Initial formation of an N-halogenated sulfamate followed by Rh-mediated homolysis generates an N-centered radical, which serves as the active oxidant.

Graphical abstract: Site-selective bromination of sp3 C–H bonds

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Supplementary files

Article information


Submitted
25 Oct 2017
Accepted
18 Nov 2017
First published
20 Nov 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 100-104
Article type
Edge Article

Site-selective bromination of sp3 C–H bonds

S. Sathyamoorthi, S. Banerjee, J. Du Bois, N. Z. Burns and R. N. Zare, Chem. Sci., 2018, 9, 100
DOI: 10.1039/C7SC04611A

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