Exploiting the Hydrogen-Bonding Capacity of Organoboronic Acids to Direct Covalent Bond Formation in the Solid State: Templation and Catalysis of the [2 + 2] Photodimerization

The ability of organoboronic acids to direct intermolecular [2 + 2] photodimerizations in the solid state is identified. The reactivity of 1,2-bis­(4-pyridyl)­ethylene (bpe) within cocrystals of discrete hydrogen-bonded molecular assemblies generates rctt-tetrakis­(4-pyridyl)­cyclobutane (tpcb) ster...

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Bibliographic Details
Published in:Organic letters 2018-09, Vol.20 (17), p.5490-5492
Main Authors: Campillo-Alvarado, Gonzalo, Brannan, Alexis D, Swenson, Dale C, MacGillivray, Leonard R
Format: Article
Language:English
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Summary:The ability of organoboronic acids to direct intermolecular [2 + 2] photodimerizations in the solid state is identified. The reactivity of 1,2-bis­(4-pyridyl)­ethylene (bpe) within cocrystals of discrete hydrogen-bonded molecular assemblies generates rctt-tetrakis­(4-pyridyl)­cyclobutane (tpcb) stereoselectively and in up to quantitative yield. Dry grinding of the boronic acids and excess bpe reveal the acids to function as supramolecular catalysts.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02439