底物诱导的离子合作催化：使用碳酸二甲酯的吲哚衍生物的双官能化

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC The Journal of Organic Chemistry Pub Date : 2024-10-21 DOI:10.1021/acs.joc.4c01619

Sangita Dattatray Shinde, Ashik Chhetri, Sayak Ghosh, Anusri Debnath, Pooja Joshi, Dinesh Kumar

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引用次数: 0

摘要

随着全球对采用可持续化学的迫切需求，开发出了更多以阶跃经济方式使用二氧化碳和二氧化碳衍生化学品的无害环境策略（EBS）。在此背景下，我们研究了在催化量 Cs2CO3 的存在下，使用碳酸二甲酯（DMC）对吲哚衍生物进行 C-H 甲基化和（C═O）甲氧基化的双重反应。其机理包括 DMF 辅助、DMC 诱导的合作离子催化，这使得 DMC 可以同时作为亲核前体和亲电前体，导致 N-苄基吲哚酮的 (C═O)- 甲氧基化和 C-H 甲基化。

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Substrate-Induced Cooperative Ionic Catalysis: Difunctionalization of Indole Derivatives Employing Dimethyl Carbonate

The global urge to adopt sustainable chemistry has resulted in the development of more environmentally benign strategies (EBS) that use CO₂ and CO₂-derived chemicals in a step-economic manner. In this context, we investigated a dual C–H methylation and (C═O)-methoxylation of indole derivatives using dimethyl carbonate (DMC) in the presence of catalytic amounts of Cs₂CO₃. Mechanistic insights include DMF-assisted, DMC-induced cooperative ionic catalysis, which allows DMC to act as both a nucleophilic and an electrophilic precursor, resulting in (C═O)-methoxylation and C–H methylation of N-benzylindolyl ketones.

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来源期刊

The Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.