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

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

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2129-2133
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	13
Issue number	7
DOIs	https://doi.org/10.1039/c4ob02160f
Publication status	Published - 2015 Feb 21
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

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.",

author = "Kazunori Miyamoto and Taiga Ota and Hoque, \{Md Mahbubul\} and Masahito Ochiai",

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AU - Miyamoto, Kazunori

AU - Ota, Taiga

AU - Hoque, Md Mahbubul

AU - Ochiai, Masahito

N1 - Publisher Copyright: © The Royal Society of Chemistry 2015.

PY - 2015/2/21

Y1 - 2015/2/21

N2 - 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.

AB - 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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UR - https://www.scopus.com/pages/publications/84922621649#tab=citedBy

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DO - 10.1039/c4ob02160f

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IS - 7

ER -

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

Abstract

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