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Issue 1, 2017
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Chromium photocatalysis: accessing structural complements to Diels–Alder adducts with electron-deficient dienophiles

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Abstract

A chromium-catalyzed, visible light-activated net [4 + 2] cycloaddition between dienes and electron-deficient alkenes is described. Gathered evidence, via control experiments, isolated intermediates, and measured redox potentials, points to several converging reaction pathways that afford the cyclohexene adducts, including a photochemical [2 + 2] cycloaddition/vinylcyclobutane rearrangement cascade and a substrate excitation/oxidation sequence to a radical cation intermediate. Notably, the accompanying mechanistic stipulations result in a process that yields regioisomeric compounds from those generated by traditional Diels–Alder cycloadditions.

Graphical abstract: Chromium photocatalysis: accessing structural complements to Diels–Alder adducts with electron-deficient dienophiles

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Supplementary files

Article information


Submitted
25 Jul 2016
Accepted
11 Sep 2016
First published
12 Sep 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 654-660
Article type
Edge Article

Chromium photocatalysis: accessing structural complements to Diels–Alder adducts with electron-deficient dienophiles

S. M. Stevenson, R. F. Higgins, M. P. Shores and E. M. Ferreira, Chem. Sci., 2017, 8, 654
DOI: 10.1039/C6SC03303B

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