Intramolecular [2 + 2] Photodimerization Achieved in the Solid State via Coordination-Driven Self-Assembly

An intramolecular [2 + 2] photocycloaddition is achieved in the organic solid state via self-assembly of Ag­(I) ions and an endo-ditopic bipyridine. The cations aide to organize carbon–carbon double (CC) bonds attached to the bipyridine for the cycloaddition reaction. The CC bonds react regioselec...

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Bibliographic Details
Published in:Organic letters 2015-07, Vol.17 (13), p.3233-3235
Main Authors: Laird, Rebecca C, Sinnwell, Michael A, Nguyen, Nam P, Swenson, Dale C, Mariappan, S. V. Santhana, MacGillivray, Leonard R
Format: Article
Language:English
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Summary:An intramolecular [2 + 2] photocycloaddition is achieved in the organic solid state via self-assembly of Ag­(I) ions and an endo-ditopic bipyridine. The cations aide to organize carbon–carbon double (CC) bonds attached to the bipyridine for the cycloaddition reaction. The CC bonds react regioselectively and quantitatively to afford a photoproduct with edge-sharing four-, five-, and six-membered rings. Our study demonstrates the first use of a metal–organic template to direct an intramolecular [2 + 2] photodimerization in the organic solid state.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b00527