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. 2011 Dec 7;133(48):19350-3.
doi: 10.1021/ja2093579. Epub 2011 Nov 11.

Radical cation Diels-Alder cycloadditions by visible light photocatalysis

Shishi Lin  1 , Michael A Ischay, Charles G Fry, Tehshik P Yoon
Affiliations

Radical cation Diels-Alder cycloadditions by visible light photocatalysis

Shishi Lin et al. J Am Chem Soc. .

Abstract

Ruthenium(II) polypyridyl complexes promote the efficient radical cation Diels-Alder cycloaddition of electron-rich dienophiles upon irradiation with visible light. These reactions enable facile [4 + 2] cycloadditions that would be electronically mismatched under thermal conditions. Key to the success of this methodology is the availability of ligand-modified ruthenium complexes that enable rational tuning of the electrochemical properties of the catalyst without significantly perturbing the overall photophysical properties of the system.

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Figures

Chart 1
Chart 1
Scope of the radical cation Diels–Alder cycloadditiona
Scheme 1
Scheme 1
Proposed mechanism
Scheme 2
Scheme 2
Synthetic studies on heitziamide A
See this image and copyright information in PMC

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