Contrasting frustrated Lewis pair reactivity with selenium- and boron-based Lewis acids

Wilkins, Lewis C., Gunther, Benjamin A. R., Walther, Melanie, Lawson, James R., Wirth, Thomas ORCID: https://orcid.org/0000-0002-8990-0667 and Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831 2016. Contrasting frustrated Lewis pair reactivity with selenium- and boron-based Lewis acids. Angewandte Chemie International Edition 55 (37) , pp. 11292-11295. 10.1002/anie.201605239

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Abstract

The activation of π‐bonds in diynyl esters has been investigated by using soft and hard Lewis acids. In the case of the soft selenium Lewis acid PhSeCl, sequential activation of the alkyne bonds leads initially to an isocoumarin (1 equiv PhSeCl) and then to a tetracyclic conjugated structure with the isocoumarin subunit fused to a benzoselenopyran (3 equiv PhSeCl). Conversely, the reaction with the hard Lewis acidic borane B(C6F5)3 initiates a cascade reaction to yield a complex π‐conjugated system containing phthalide and indene subunits.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Additional Information:	PDF uploaded in accordance with publisher's policies at http://www.sherpa.ac.uk/romeo/issn/1433-7851/ (accessed 4.8.16).
Publisher:	Wiley
ISSN:	1433-7851
Funders:	EPSRC
Date of First Compliant Deposit:	4 August 2016
Date of Acceptance:	3 August 2016
Last Modified:	11 May 2023 16:49
URI:	https://orca.cardiff.ac.uk/id/eprint/93594

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