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Transition-metal-free radical relay cyclization of vinyl azides with 1,4-dihydropyridines involving a 1,5-hydrogen-atom transfer: access to α-tetralone scaffolds

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Abstract

The remote C(sp3)–H functionalization enabled by a radical-mediated 1,5-hydrogen-atom transfer (HAT) process using vinyl azides and 1,4-dihydropyridines as precursors has been described. In this study, 1,4-dihydropyridines can function as 1,2-diradical synthons through sequential homolytic cleavage of an ipso-C–C bond and a β-C(sp3)–H bond. This reaction offers facile access to a diverse range of α-tetralones with excellent stereoselectivity. The utility of the present method is further highlighted by its application to rapid assembly of the tetracyclic scaffold present in furanosteroids as well as the synthesis of aromatic amines.

Graphical abstract: Transition-metal-free radical relay cyclization of vinyl azides with 1,4-dihydropyridines involving a 1,5-hydrogen-atom transfer: access to α-tetralone scaffolds

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Article information


Submitted
31 Aug 2020
Accepted
06 Oct 2020
First published
08 Oct 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Transition-metal-free radical relay cyclization of vinyl azides with 1,4-dihydropyridines involving a 1,5-hydrogen-atom transfer: access to α-tetralone scaffolds

Y. Liao, Y. Ran, G. Liu, P. Liu and X. Liu, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO01042A

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