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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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Publication details

The article was received on 25 Jul 2016, accepted on 11 Sep 2016 and first published on 12 Sep 2016


Article type: Edge Article
DOI: 10.1039/C6SC03303B
Citation: Chem. Sci., 2017,8, 654-660
  • Open access: Creative Commons BY license
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    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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