Issue 32, 2018

Photocatalytic reverse polarity Povarov reaction

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY license

Chem. Sci., 2018,9, 6653-6658

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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