Solvent-controlled catalytic divergent C–H alkylation of quinolones driven by unusual DMSO-promoted 1,3-heteroarene migration

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-12-26 DOI:10.1039/d4qo01980f

Ye Lim Kim, Yuri Yun, Seoung-Mi Choi, Ju Hyun Kim

引用次数: 0

Abstract

We report on a catalytic divergent C–H alkylation of 4-quinolones with diazo compounds where the reaction pathways are controlled by a reaction solvent. Cp*Rh(III)-catalyzed site-selective C−H alkylation was carried out in dichloromethane to produce C2-alkylated 4-quinolones. C(2)−H alkylation and sequential [1,3]-heteroarene rearrangement were achieved by utilizing EtOH/DMSO solvent in the same catalytic system at 70°C, allowing valuable 4-quinolones bearing an all-carbon quaternary center at the 2-position to be efficiently synthesized in a one-pot operation. By combining experimental results and computational studies, we propose an unprecedented DMSO-promoted Truce-Smiles rearrangement.

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.