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Contrasting Frustrated Lewis Pair Reactivity with Selenium- and Boron-Based Lewis Acids.

ABSTRACT: The activation of ?-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(C6 F5 )3 initiates a cascade reaction to yield a complex ?-conjugated system containing phthalide and indene subunits.

SUBMITTER: Wilkins LC

PROVIDER: S-EPMC5113806 | biostudies-literature | 2016 Sep

REPOSITORIES: biostudies-literature

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Contrasting Frustrated Lewis Pair Reactivity with Selenium- and Boron-Based Lewis Acids.

Wilkins Lewis C LC Günther Benjamin A R BA Walther Melanie M Lawson James R JR Wirth Thomas T Melen Rebecca L RL

Angewandte Chemie (International ed. in English) 20160803 37

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(C6 F5 )3 initiates a cascade reaction to yield a complex π-conjugated s ...[more]

PMID: 27484052

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