Substrate-Induced Cooperative Ionic Catalysis: Difunctionalization of Indole Derivatives Employing Dimethyl Carbonate DOI
Sangita Dattatray Shinde,

Asma Poudel Chhetri,

Sayak Ghosh

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15995 - 16003

Published: Oct. 21, 2024

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 a step-economic manner. In this context, we investigated dual C–H methylation (C═O)-methoxylation indole derivatives using dimethyl carbonate (DMC) presence catalytic amounts Cs2CO3. Mechanistic insights include DMF-assisted, DMC-induced cooperative ionic catalysis, which allows DMC act as both nucleophilic an electrophilic precursor, resulting N-benzylindolyl ketones.

Language: Английский

Boron-Catalyzed Formylation of Indoles Using Trimethyl Orthoformate as Carbonyl Source DOI Creative Commons

Kiratipong Charoensawas,

Jirapat Yimyaem,

Uthaiwan Sirion

et al.

ACS Omega, Journal Year: 2025, Volume and Issue: 10(20), P. 20497 - 20508

Published: May 14, 2025

This study presents a practical, efficient, and scalable approach for the C-H formylation of indoles their derivatives using alkyl orthoesters as formylating agents. Boron trifluoride diethyl etherate (BF3·OEt2) was found to be an effective stoichiometric catalyst, with trimethyl orthoformate (TMOF) acting reliable formyl source. method enables rapid efficient synthesis wide range C-formylindoles, including C3, C2, C6, C7 derivatives, well electron-rich aromatic carbaldehydes. Key advantages protocol include its operational simplicity, use inexpensive readily available reagents, neat conditions, ambient reaction temperatures, short times (typically 1-5 min), broad substrate tolerance, scalability. These features make highly versatile suitable diverse synthetic applications.

Language: Английский

Citations

0
Copper-Catalyzed Oxidative Synthesis of 3-Aryl-5-fluoroalkyl-1,3,4-oxadiazol-2(3H)-ones Using Perfluorocarboxylic Anhydride as a Reagent DOI
Jiaqing Lu,

Shouxiong Chen,

Minze Wu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 25, 2024

A copper-catalyzed oxidative annulation of sydnones with perfluorocarboxylic anhydride for the synthesis 3-aryl-5-fluoroalkyl-1,3,4-oxadiazol-2(3

Language: Английский

Citations

0
Substrate-Induced Cooperative Ionic Catalysis: Difunctionalization of Indole Derivatives Employing Dimethyl Carbonate DOI
Sangita Dattatray Shinde,

Asma Poudel Chhetri,

Sayak Ghosh

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15995 - 16003

Published: Oct. 21, 2024

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 a step-economic manner. In this context, we investigated dual C–H methylation (C═O)-methoxylation indole derivatives using dimethyl carbonate (DMC) presence catalytic amounts Cs2CO3. Mechanistic insights include DMF-assisted, DMC-induced cooperative ionic catalysis, which allows DMC act as both nucleophilic an electrophilic precursor, resulting N-benzylindolyl ketones.

Language: Английский

Citations

0