Journal article
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
Organic letters, Vol.20(17), pp.5490-5492
09/07/2018
DOI: 10.1021/acs.orglett.8b02439
PMID: 30129766
Abstract
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.
Details
- Title: Subtitle
- 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
- Creators
- Gonzalo Campillo-Alvarado - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United StatesAlexis D Brannan - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United StatesDale C Swenson - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United StatesLeonard R MacGillivray - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United States
- Resource Type
- Journal article
- Publication Details
- Organic letters, Vol.20(17), pp.5490-5492
- DOI
- 10.1021/acs.orglett.8b02439
- PMID
- 30129766
- ISSN
- 1523-7060
- eISSN
- 1523-7052
- Grant note
- DOI: 10.13039/501100003141, name: Consejo Nacional de Ciencia y Tecnolog?a; DOI: 10.13039/100008893, name: University of Iowa; DOI: 10.13039/100000078, name: Division of Materials Research, award: DMR-1708673
- Language
- English
- Date published
- 09/07/2018
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Chemistry
- Record Identifier
- 9984216571102771
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