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Single-Crystal-to-Single-Crystal [2 + 2] Photodimerization Involving B←N Coordination with Generation of a Thiophene Host

Cite this: Organometallics 2020, 39, 12, 2197–2201
Publication Date (Web):June 8, 2020
https://doi.org/10.1021/acs.organomet.0c00258
Copyright © 2020 American Chemical Society

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    Abstract

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    We report on B←N coordination to support a single-crystal-to-single-crystal reaction in the solid state. A [2 + 2] photodimerization is achieved with face-to-face π-stacks of monotopic B←N adducts composed of a phenylboronic acid catechol ester and an alkene with a terminal thiophene group. The photoreaction generates a ditopic B-adduct involving a head-to-tail cyclobutane regio- and stereoselectively. The photodimerization is accompanied by an increase in the tetrahedral character of the B atom. The resulting boron enables channel confinement of chloroform upon recrystallization.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.organomet.0c00258.

    • Experimental information, PXRD patterns, and additional SCXRD data (PDF)

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    CCDC 19933661993369 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    This article is cited by 17 publications.

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