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Regioselective Pd-Catalyzed Carbopalladation/Decarboxylative Allylic Alkynylation of ortho -Iodoallenamides with Alkynyl Carboxylic Acids

Abstract : A regioselective Pd-catalyzed domino carbopalladation/decarboxylative allylic alkynylation of ortho-iodoallenamides with alkynyl carboxylic acids was studied. This domino process, based on the consecutive formation of C(sp2)–C(sp2) and C(sp3)–C(sp) bonds, was originally achieved for the design of a novel library of prop-2-ynyl isoquinolinones and then extended to indoles. Finally, a general three-step one-pot strategy involving in situ generation of allenamide, π-allyl-Pd complex formation, and decarboxylative allylic alkynylation was subsequently set up.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02282525
Contributor : Madeleine Roux-Merlin <>
Submitted on : Tuesday, September 10, 2019 - 9:54:12 AM
Last modification on : Thursday, July 2, 2020 - 3:29:48 AM

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Jonathan Hédouin, Vincent Carpentier, Romain Renard, Cédric Schneider, Isabelle Gillaizeau, et al.. Regioselective Pd-Catalyzed Carbopalladation/Decarboxylative Allylic Alkynylation of ortho -Iodoallenamides with Alkynyl Carboxylic Acids. Journal of Organic Chemistry, American Chemical Society, 2019, 84 (16), pp.10535-10545. ⟨10.1021/acs.joc.9b01408⟩. ⟨hal-02282525⟩

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