Journal article
Opportunities Using Boron to Direct Reactivity in the Organic Solid State
Synlett, Vol.32(7), pp.655-662
04/22/2021
DOI: 10.1055/s-0040-1707297
Abstract
Abstract
This Account describes work by our research group that highlights opportunities to utilize organoboron molecules to direct chemical reactivity in the organic solid state. Specifically, we convey a previously unexplored use of hydrogen bonding of boronic acids and boron coordination in boronic esters to achieve [2+2]-photocycloadditions in crystalline solids. Organoboron molecules act as templates or ‘shepherds’ to organize alkenes in a suitable geometry to undergo regio- and stereoselective [2+2]-photocycloadditions in quantitative yields. We also provide a selection of publications that served as an inspiration for our strategies and offer challenges and opportunities for future developments of boron in the field of materials and solid-state chemistry.
1 Introduction
1.1 Template Strategy for [2+2]-Photocycloadditions in the Solid State
2 Boronic Acids as Templates for [2+2]-Photocycloadditions in the Solid State
2.1 Supramolecular Catalysis of [2+2]-Photocycloadditions in the Solid State Using Boronic Acids
3 Boronic Esters as Templates for [2+2]-Photocycloadditions in the Solid State
3.1 Application of Photoproducts: Separation of Thiophene from Benzene through Crystallization
3.2 Crystal Reactivity of B←N-Bonded Adducts: The Case of Styrylthiophenes
4 Conclusions and Perspectives
Details
- Title: Subtitle
- Opportunities Using Boron to Direct Reactivity in the Organic Solid State
- Creators
- Gonzalo Campillo-AlvaradoLeonard R MacGillivray - Department of Chemistry, University of Iowa
- Resource Type
- Journal article
- Publication Details
- Synlett, Vol.32(7), pp.655-662
- Publisher
- Georg Thieme Verlag KG
- DOI
- 10.1055/s-0040-1707297
- ISSN
- 0936-5214
- eISSN
- 1437-2096
- Grant note
- Consejo Nacional de Ciencia y Tecnología DMR-1708673 / Division of Materials Research CHE-1828117 / Division of Chemistry
- Language
- English
- Date published
- 04/22/2021
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Chemistry
- Record Identifier
- 9984216593302771
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