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Photocatalytic decarboxylative [2 + 2 + 1] annulation of 1,6-enynes with N-hydroxyphthalimide esters for the synthesis of indene-containing polycyclic compounds

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Abstract

An efficient photoredox-mediated [2 + 2 + 1] cascade annulation of 1,6-enynes with N-hydroxyphthalimide esters was reported for the synthesis of a series of indene-containing polycyclic frameworks through a sequence of radical addition, 5-exo-dig cyclization, 1,n-H shift and 5-endo-trig cyclization. This protocol exhibits excellent functional group tolerance for establishing spiro and non-spiro polycyclic architectures under mild conditions. Moreover, this transformation could also be achieved smoothly via a simple phosphine/iodide-based photoredox system.

Graphical abstract: Photocatalytic decarboxylative [2 + 2 + 1] annulation of 1,6-enynes with N-hydroxyphthalimide esters for the synthesis of indene-containing polycyclic compounds

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Publication details

The article was received on 22 Sep 2019, accepted on 16 Oct 2019 and first published on 16 Oct 2019


Article type: Research Article
DOI: 10.1039/C9QO01166H
Org. Chem. Front., 2019, Advance Article

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    Photocatalytic decarboxylative [2 + 2 + 1] annulation of 1,6-enynes with N-hydroxyphthalimide esters for the synthesis of indene-containing polycyclic compounds

    M. Jiao, D. Liu, X. Hu and P. Xu, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO01166H

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