Rh(iii)-Catalyzed tandem C(sp2)–H allylation/N-alkylation annulation of arene amides with 2-alkylidenetrimethylene carbonates

文献情報

出版日 2021-10-08

DOI 10.1039/D1QO01129D

インパクトファクター 5.281

著者

Hui Xie, Jin-Yi Liang, Zhuo-Jun Huang, Bing Shu, Yi-Chuan Zheng, Yan-Zhi Liu, Shao-Yong Chen, Xu-Ge Liu, Shang-Shi Zhang

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要旨

A Rh(III)-catalyzed tandem C(sp2)–H allylation/N-alkylation annulation reaction of arene amides employing 5-methylene-1,3-dioxan-2-one as an efficient allyl source has been disclosed for the first time, affording an unprecedented opportunity for the synthesis of 3,4-dihydropyrimido[1,6-a]indol-1(2H)-ones in moderate to excellent yields. Meanwhile, Rh(III)-catalyzed C(sp2)–H allylation products can also be obtained under altered reaction conditions. These practical and scalable divergent synthesis protocols proceeded smoothly under mild reaction conditions. Broad substrate scope, good functional group compatibility and total 32 examples were observed. Moreover, the preliminary mechanism studies show that the rhodium catalyst plays a dual role in the C–H activation and N-alkylation annulation process.

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

Rh(iii)-Catalyzed tandem C(sp2)–H allylation/N-alkylation annulation of arene amides with 2-alkylidenetrimethylene carbonates

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