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Contrasting Frustrated Lewis Pair Reactivity with Selenium‐ and Boron‐Based Lewis Acids
Author(s) -
Wilkins Lewis C.,
Günther Benjamin A. R.,
Walther Melanie,
Lawson James R.,
Wirth Thomas,
Melen Rebecca L.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201605239
Subject(s) - frustrated lewis pair , lewis acids and bases , isocoumarin , chemistry , boranes , borane , conjugated system , reactivity (psychology) , adduct , polymer chemistry , phthalide , boron , medicinal chemistry , stereochemistry , organic chemistry , catalysis , medicine , polymer , alternative medicine , pathology
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(C 6 F 5 ) 3 initiates a cascade reaction to yield a complex π‐conjugated system containing phthalide and indene subunits.