One-pot cross-enyne metathesis (CEYM)-Diels-Alder reaction of gem-difluoropropargylic alkynes

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Abstract

Propargylic difluorides 1 were used as starting substrates in a combination of cross-enyne metathesis and Diels-Alder reactions. Thus, the reaction of 1 with ethylene in the presence of 2nd generation Hoveyda-Grubbs catalyst generates a diene moiety which in situ reacts with a wide variety of dienophiles giving rise to a small family of new fluorinated carbo- and heterocyclic derivatives in moderate to good yields. This is a complementary protocol to the one previously described by our research group, which involved the use of 1,7-octadiene as an internal source of ethylene. © 2013 Fustero et al; licensee Beilstein-Institut.

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Fustero, S., Bello, P., Miró, J., Sánchez-Roselló, M., Haufe, G., & Del Pozo, C. (2013). One-pot cross-enyne metathesis (CEYM)-Diels-Alder reaction of gem-difluoropropargylic alkynes. Beilstein Journal of Organic Chemistry, 9, 2688–2695. https://doi.org/10.3762/bjoc.9.305

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