Remote methylene C(sp3)–H functionalization enabled by organophosphine-catalyzed alkyne isomerization

文献情報

出版日 2020-12-09

DOI 10.1039/D0QO01399D

インパクトファクター 5.281

著者

Zefeng Song, Jianyu Zhang

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要旨

A remote δ methylene C(sp3)–H functionalization catalyzed by an organophosphine through an alkyne isomerization/conjugate addition cascade was discovered. No classical electron-withdrawing group is required to pre-activate the aryl alkyne, which will undergo isomerization to its corresponding diene under only 10 mol% of PMe2Ph with a catalytic proton shuttle. The phosphoryl ylide was postulated as a key intermediate and different electrophiles were used to trap the vinylogous ylide that resulted in a large group of δ C(sp3)–H functionalized products (>60 examples, yields up to 99%) with good diastereoselectivity. Mechanistic studies were carried out and a catalytic cycle was proposed based on deuterium-labeling experiments. The conjugated polyene products were investigated for their fluorescence properties.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Remote methylene C(sp3)–H functionalization enabled by organophosphine-catalyzed alkyne isomerization

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