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

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

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 o...

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Veröffentlicht in:Journal of organic chemistry 2019-08, Vol.84 (16), p.10535-10545
Hauptverfasser: Hédouin, Jonathan, Carpentier, Vincent, Renard, Romain M. Q, Schneider, Cédric, Gillaizeau, Isabelle, Hoarau, Christophe
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container_end_page 10545
container_issue 16
container_start_page 10535
container_title Journal of organic chemistry
container_volume 84
creator Hédouin, Jonathan
Carpentier, Vincent
Renard, Romain M. Q
Schneider, Cédric
Gillaizeau, Isabelle
Hoarau, Christophe
description 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.
doi_str_mv 10.1021/acs.joc.9b01408
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title Regioselective Pd-Catalyzed Carbopalladation/Decarboxylative Allylic Alkynylation of ortho-Iodoallenamides with Alkynyl Carboxylic Acids
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