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Issue 32, 2018
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Photocatalytic reverse polarity Povarov reaction

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Abstract

A visible light mediated iridium photocatalysed reverse polarity Povarov reaction of aryl imines and electron deficient alkenes is described. Operating via a putative nucleophilic α-amino radical, generated by a proton coupled electron transfer process, addition to a range of conjugated electron deficient alkene substrates affords substituted tetrahydroquinoline products in high yields and with typically good to excellent diastereoselectivity in favor of the trans diastereoisomer. Sub-stoichiometric quantities of Hantzsch ester were found to be key to initiate the overall redox-neutral, free radical cyclization cascade. This new reaction complements existing two electron Lewis acid mediated variants and expands the capabilities of imine umpolung chemistry to synthetically relevant cyclisation methodology.

Graphical abstract: Photocatalytic reverse polarity Povarov reaction

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Supplementary files

Article information


Submitted
13 Apr 2018
Accepted
06 Jul 2018
First published
06 Jul 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, 6653-6658
Article type
Edge Article

Photocatalytic reverse polarity Povarov reaction

J. A. Leitch, Angel L. Fuentes de Arriba, J. Tan, O. Hoff, C. M. Martínez and D. J. Dixon, Chem. Sci., 2018, 9, 6653
DOI: 10.1039/C8SC01704B

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