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Synthesis of alkenyl boronates from allyl-substituted aromatics using an olefin cross-metathesis protocol.

Abstract : An efficient synthesis of 3-aryl-1-propenyl boronates from pinacol vinyl boronic ester and allyl-substituted aromatics by cross metathesis is reported. Although the allylbenzene derivatives are prone to isomerization reaction under metathesis conditions, we found that some ruthenium catalysts are effective for this methodology. This strategy thus provides an interesting alternative approach to alkyne hydroboration, leading to the preparation of unknown compounds. Moreover, the boron substituent can be replaced by various functional groups in good yields.
Keywords : metathesis boronic
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-00861076
Contributor : Bertrand Carboni <>
Submitted on : Wednesday, September 11, 2013 - 6:23:09 PM
Last modification on : Thursday, March 5, 2020 - 2:05:38 PM

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Rémy Hemelaere, François Carreaux, Bertrand Carboni. Synthesis of alkenyl boronates from allyl-substituted aromatics using an olefin cross-metathesis protocol.. Journal of Organic Chemistry, American Chemical Society, 2013, 78 (13), pp.6786-92. ⟨10.1021/jo400872x⟩. ⟨hal-00861076⟩

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