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Issue 11, 2018
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Intramolecular hydride transfer onto arynes: redox-neutral and transition metal-free C(sp3)–H functionalization of amines

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Abstract

Transition metal-free intramolecular hydride transfer onto arynes is reported for the first time. This unique transformation is utilized in redox-neutral intermolecular α-functionalization reactions of different tertiary amines, generating C(sp3)–C(sp3/sp2/sp) bonds in a single synthetic operation. Deuterium labeling studies support initial cleavage of the α-C–H bond via intramolecular 1,5-hydride transfer onto the aryne, which leads to activation of a range of integrated pronucleophiles and ultimately affords a new approach to cross-dehydrogenative coupling reactions which utilize aryne intermediates.

Graphical abstract: Intramolecular hydride transfer onto arynes: redox-neutral and transition metal-free C(sp3)–H functionalization of amines

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Article information


Submitted
12 Jan 2018
Accepted
07 Feb 2018
First published
08 Feb 2018

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, 2873-2878
Article type
Edge Article

Intramolecular hydride transfer onto arynes: redox-neutral and transition metal-free C(sp3)–H functionalization of amines

F. I. M. Idiris, C. E. Majesté, G. B. Craven and C. R. Jones, Chem. Sci., 2018, 9, 2873
DOI: 10.1039/C8SC00181B

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