钴催化 2-(1-甲基肼基)吡啶辅助的 C-H 烷基化/环化反应：反应机理的深入研究和快速构建环戊并[ ]异喹啉酮衍生物。
Cobalt-Catalyzed 2-(1-Methylhydrazinyl)pyridine-Assisted C-H Alkylation/Annulation: Mechanistic Insights and Rapid Access to Cyclopenta[]isoquinolinone Derivatives.
机构信息
The Key Laboratory of Chemical Genomics and Lab of Computational Chemistry and Drug Design, The State Key Laboratory of Chemical Oncogenomics, Shenzhen Graduate School of Peking University, Shenzhen 518055, China.
Department of Chemistry, Guangdong University of Education, Guangzhou 510303, China.
出版信息
J Org Chem. 2021 Nov 5;86(21):14915-14927. doi: 10.1021/acs.joc.1c01658. Epub 2021 Sep 27.
We have developed cobalt-catalyzed, bidentate 2-(1-methylhydrazinyl)pyridine (MHP)-directed C()-H alkylation/annulation of benzoic hydrazides with various alkenes. Notably, diverse cyclopenta[]isoquinolinones and dihydroisoquinolinones were obtained via this functional group-tolerant protocol. The reaction can be performed on a gram scale while maintaining an excellent yield, and the directing group can be removed efficiently under mild conditions. Furthermore, density-functional theory (DFT) calculations provide an incisive understanding of the observed regioselectivities for different olefins.
我们开发了钴催化、双齿 2-(1-甲基肼基)吡啶（MHP）导向的苯甲酸酰肼与各种烯烃的 C()-H 烷基化/环化反应。值得注意的是，通过这种官能团耐受性的方法，可以得到多种环戊[]异喹啉酮和二氢异喹啉酮。该反应可以在克级规模下进行，同时保持优异的收率，并且在温和条件下可以有效地去除导向基团。此外，密度泛函理论（DFT）计算为不同烯烃的观察到的区域选择性提供了深刻的理解。
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