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A New Catalytic Route to Boryl- and Borylsilyl-Substituted Buta-1,3-dienes

✍ Scribed by Jȩdrzej Walkowiak; Magdalena Jankowska-Wajda; Bogdan Marciniec

Publisher: John Wiley and Sons
Year: 2008
Tongue: English
Weight: 297 KB
Volume: 14
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.200800518

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✦ Synopsis

Abstract

Vinyl‐substituted boronates in the presence of complexes containing RuH bonds (preferably [Ru(CO)ClH(PCy~3~)~2~], Cy: cyclohexyl) react regioselectively with terminal ethynes (involving silylethynes), albeit with the exception of phenylacetylene, to produce boryl‐ and borylsilyl‐substituted buta‐1,3‐dienes with a preference for E,E‐diene. The reaction opens a new catalytic route for the preparation of dienylboronates, and particularly dienylsilylboronates, that are functionalised building blocks in the synthesis of organic and natural products. The mechanism of this new reaction was proved to involve an insertion of alkyne into RuH bonds followed by an insertion of coordinated vinyl boronate into the RuC bond and β‐hydrogen transfer to the metal to eliminate boryldiene or borylsilyldiene.

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