期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 37, 页码 11292-11295出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201605239
关键词
annulation; cyclization; domino reactions; frustrated Lewis pairs; main-group elements
资金
- Engineering and Physical Sciences Research Council [EP/N02320X/1] Funding Source: researchfish
- EPSRC [EP/N02320X/1] Funding Source: UKRI
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 (1equiv PhSeCl) and then to a tetracyclic conjugated structure with the isocoumarin subunit fused to a benzoselenopyran (3equiv PhSeCl). Conversely, the reaction with the hard Lewis acidic borane B(C6F5)(3) initiates a cascade reaction to yield a complex -conjugated system containing phthalide and indene subunits.
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