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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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Publication details

The article was received on 12 Jan 2018, accepted on 07 Feb 2018 and first published on 08 Feb 2018


Article type: Edge Article
DOI: 10.1039/C8SC00181B
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
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    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, Advance Article , DOI: 10.1039/C8SC00181B

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