Synthesis of Allenes by Hydroalkylation of 1,3-Enynes with Ketones Enabled by Cooperative Catalysis.

Eaton, Maxwell; Dai, Yuping; Wang, Ziyong; Li, Bo; Lamine, Walid; Miqueu, Karinne; Liu, Shih-Yuan

Eaton, Maxwell; Dai, Yuping; Wang, Ziyong; Li, Bo; Lamine, Walid; Miqueu, Karinne; Liu, Shih-Yuan.

Afiliación

Eaton M; Department of Chemistry, Boston College, Chestnut Hill, Massachusetts 02467-3860, United States.
Dai Y; E2S UPPA/CNRS, Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux IPREM UMR 5254, Université de Pau et des Pays de l'Adour, Hélioparc, 2 avenue P. Angot, 64053 Pau Cedex 09, France.
Wang Z; Department of Chemistry, Boston College, Chestnut Hill, Massachusetts 02467-3860, United States.
Li B; Department of Chemistry, Boston College, Chestnut Hill, Massachusetts 02467-3860, United States.
Lamine W; E2S UPPA/CNRS, Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux IPREM UMR 5254, Université de Pau et des Pays de l'Adour, Hélioparc, 2 avenue P. Angot, 64053 Pau Cedex 09, France.
Miqueu K; E2S UPPA/CNRS, Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux IPREM UMR 5254, Université de Pau et des Pays de l'Adour, Hélioparc, 2 avenue P. Angot, 64053 Pau Cedex 09, France.
Liu SY; Department of Chemistry, Boston College, Chestnut Hill, Massachusetts 02467-3860, United States.

J Am Chem Soc ; 145(39): 21638-21645, 2023 Oct 04.

Article en En | MEDLINE | ID: mdl-37738372

RESUMEN

A method for the synthesis of allenes by the addition of ketones to 1,3-enynes by cooperative Pd(0)Senphos/B(C6F5)3/NR3 catalysis is described. A wide range of aryl- and aliphatic ketones undergo addition to various 1,3-enynes in high yields at room temperature. Mechanistic investigations revealed a rate-determining outer-sphere proton transfer mechanism, which was corroborated by DFT calculations.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Am Chem Soc Año: 2023 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Estados Unidos

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