Issue 23, 2019

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
22 sep. 2019
Accepted
16 oct. 2019
First published
16 oct. 2019

Org. Chem. Front., 2019,6, 3834-3838

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, 6, 3834 DOI: 10.1039/C9QO01166H

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