Transition metal free C-N bond forming dearomatizations and aryl C-H aminations by in situ release of a hydroxylamine-based aminating agent

Joshua Farndon; Xiao-Feng Ma; John Bower

doi:10.1021/jacs.7b07830

Transition metal free C-N bond forming dearomatizations and aryl C-H aminations by in situ release of a hydroxylamine-based aminating agent

Joshua Farndon, Xiao-Feng Ma, John Bower

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Abstract

We outline a simple protocol that accesses directly unprotected secondary amines by intramolecular C–N bond forming dearomatization or aryl C–H amination. The method is dependent on the generation of a potent electrophilic aminating agent released by in situ deprotection of O-Ts activated N-Boc hydroxylamines.

Original language	English
Pages (from-to)	14005-14008
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	40
Early online date	27 Sep 2017
DOIs	https://doi.org/10.1021/jacs.7b07830
Publication status	Published - 11 Oct 2017

Structured keywords

BCS and TECS CDTs

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2 Finished

A 13C NMR Coldprobe to Underpin Chemistry Research.
Butts, C. P.
28/02/14 → 29/11/17
Project: Research
3-month Core Capability for Chemistry Research
Crosby, J.
1/01/13 → 1/04/13
Project: Research

Cite this

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title = "Transition metal free C-N bond forming dearomatizations and aryl C-H aminations by in situ release of a hydroxylamine-based aminating agent",

abstract = "We outline a simple protocol that accesses directly unprotected secondary amines by intramolecular C–N bond forming dearomatization or aryl C–H amination. The method is dependent on the generation of a potent electrophilic aminating agent released by in situ deprotection of O-Ts activated N-Boc hydroxylamines.",

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PY - 2017/10/11

Y1 - 2017/10/11

N2 - We outline a simple protocol that accesses directly unprotected secondary amines by intramolecular C–N bond forming dearomatization or aryl C–H amination. The method is dependent on the generation of a potent electrophilic aminating agent released by in situ deprotection of O-Ts activated N-Boc hydroxylamines.

AB - We outline a simple protocol that accesses directly unprotected secondary amines by intramolecular C–N bond forming dearomatization or aryl C–H amination. The method is dependent on the generation of a potent electrophilic aminating agent released by in situ deprotection of O-Ts activated N-Boc hydroxylamines.

U2 - 10.1021/jacs.7b07830

DO - 10.1021/jacs.7b07830

M3 - Article (Academic Journal)

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SN - 0002-7863

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Transition metal free C-N bond forming dearomatizations and aryl C-H aminations by in situ release of a hydroxylamine-based aminating agent

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Projects

A 13C NMR Coldprobe to Underpin Chemistry Research.

3-month Core Capability for Chemistry Research

Cite this