Metal-free C–H amination of unactivated hydrocarbons with sulfonylimino-λ3-bromanes generated in situ from (diacetoxybromo)benzene

Kazunori Miyamoto; Taiga Ota; Md. Mahbubul Hoque; Masahito Ochiai

doi:10.1039/C4OB02160F

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Metal-free C–H amination of unactivated hydrocarbons with sulfonylimino-λ³-bromanes generated in situ from (diacetoxybromo)benzene†

Kazunori Miyamoto,*^ab Taiga Ota,^c Md. Mahbubul Hoque^c and Masahito Ochiai^c

Author affiliations

* Corresponding authors

^a Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-12 Hongo, Bunkyo-ku, Tokyo, Japan
E-mail: kmiya@mol.f.u-tokyo.ac.jp

^b Advanced Elements Chemistry Research Team, RIKEN Center for Sustainable Resource Science, and Elements Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan

^c Graduate School of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan

Abstract

A simple method for direct metal-free C–H amination of unactivated hydrocarbons using easy-handling diacetoxy-λ³-bromane and triflylamide or sulfamate esters was developed. The high 2°/3° regioselectivities and deuterium isotope effects suggest a concerted organonitrenoid transition state, analogous to C–H amination with N-triflylimino-λ³-bromane.

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Article information

DOI: https://doi.org/10.1039/C4OB02160F
Article type: Paper
Submitted: 09 Oct 2014
Accepted: 05 Dec 2014
First published: 19 Dec 2014

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Org. Biomol. Chem., 2015,13, 2129-2133

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Metal-free C–H amination of unactivated hydrocarbons with sulfonylimino-λ³-bromanes generated in situ from (diacetoxybromo)benzene

K. Miyamoto, T. Ota, Md. M. Hoque and M. Ochiai, Org. Biomol. Chem., 2015, 13, 2129 DOI: 10.1039/C4OB02160F

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Organic & Biomolecular Chemistry