Iodine‐Assisted Regioselective C3‐H Chalcogenation of 4‐Phenyl Aminocoumarin: Access to Unusual Dual Selenylation of N‐Substituted Derivatives DOI

Suhag Singh Sahay,

S. M. Wahidur Rahaman, Ratnesh Das

et al.

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

Published: Dec. 14, 2024

Abstract A simple, efficient, metal and photocatalyst‐free, eco‐friendly approach for the C3‐H regioselective chalcogenation of 4‐phenyl aminocoumarin, as well abnormal dual selenylation N‐substituted has been developed by using diphenyl dichalcogenides iodine support in green solvent PEG‐400 under ambient temperature aerobic condition. Furthermore, amino‐2‐pyrone also accomplished similar conditions. The proposed mechanism is based on control experiments suggests an ionic pathway. reaction offers a synthetic path with high yield, methodology crucially significant due to its operational simplicity, convenient execution, scalability, tolerance various functional groups.

Language: Английский

One-pot Multicomponent Tandem Reaction for the Rapid Synthesis of 2-Amino-3-benzylindoles DOI
Pengyan Zhang, Chenrui Liu,

Maoyi Dai

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel one-pot oxidative cross-dehydrogenation coupling (CDC) reaction has been developed for the selective construction of C–N and C–C bonds at C2,3-positions indoles.

Language: Английский

Citations

0

Organoselenium-Catalyzed C2,3-Diarylation of N–H Indoles DOI
Yingying Zhang, Xiaoxiang Zhang,

Junqiu Liao

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 7216 - 7224

Published: May 2, 2024

An organoselenium-catalyzed C2,3-diarylation of unprotected N–H indoles with electron-rich aromatics has been developed. This one-pot multicomponent tandem cross-dehydrogenation coupling reaction allows for the incorporation two different aromatic groups to indoles. More importantly, this approach offers significant advantages, including a high atom and step economy, eliminating need prepreparation substrates, streamlining synthetic process enhancing its practicality. Overall, presents an efficient versatile strategy functionalization indole derivatives.

Language: Английский

Citations

3

Solvent-controlled switchable multicomponent tandem oxidative triple functionalization of indolines DOI
Xiaoxiang Zhang, Xiaoting Gu, Yingying Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 1933 - 1940

Published: Jan. 1, 2024

A new one-pot method for solvent-controlled switchable tandem oxidative triple functionalization of indolines has been developed via successive regioselective chalcogenation, oxidation, amination and halogenation.

Language: Английский

Citations

2

Iron-Catalyzed Friedel–Crafts-type 3,5-Diacylation of Indoles DOI

Xiaoting Gu,

Maoyi Dai,

Xirui Qing

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10272 - 10282

Published: July 5, 2024

The exploration of remote functionalization indoles is impeded by the inherently dominant reactivity intrinsic to pyrrole moiety. Herein, we delineate a novel strategy facilitated Lewis acid mediation, enabling C-H functionalization, which culminates in synthesis an array selectively functionalized indole derivatives, encompassing 3-trifluoroacetyl and 5-benzoyl motifs, utilizing trifluoroacetic anhydride various acyl chlorides. Notably, protocol exhibits versatility, as epitomized extension C5-acylation alkylation sulfonation reactions. This methodology distinguished its exemplary regio- chemo-selectivity, extensive substrate scope, commendable tolerance diverse functional groups, employment comparatively mild reaction conditions.

Language: Английский

Citations

2

Iron-Catalyzed C–H Arylphosphorylation of Quinoxalines DOI

Maoyi Dai,

Meilan Xu,

Xiaoting Gu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7672 - 7677

Published: Sept. 4, 2024

A one-pot strategy for iron-catalyzed C2,3-H arylphosphorylation of electron-deficient quinoxalines with phosphines and aryl compounds is reported. The proposed method features the use non-noble metal catalysts, capacity utilizing multiple as substrates, simultaneous formation C-P C-C bonds in one pot, simplicity its operation, mildness reaction conditions, compatibility a wide range substrates. Moreover, it offers practical route direct access to 2-aryl-3-phosphino

Language: Английский

Citations

2

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

Iodine‐Assisted Regioselective C3‐H Chalcogenation of 4‐Phenyl Aminocoumarin: Access to Unusual Dual Selenylation of N‐Substituted Derivatives DOI

Suhag Singh Sahay,

S. M. Wahidur Rahaman, Ratnesh Das

et al.

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

Published: Dec. 14, 2024

Abstract A simple, efficient, metal and photocatalyst‐free, eco‐friendly approach for the C3‐H regioselective chalcogenation of 4‐phenyl aminocoumarin, as well abnormal dual selenylation N‐substituted has been developed by using diphenyl dichalcogenides iodine support in green solvent PEG‐400 under ambient temperature aerobic condition. Furthermore, amino‐2‐pyrone also accomplished similar conditions. The proposed mechanism is based on control experiments suggests an ionic pathway. reaction offers a synthetic path with high yield, methodology crucially significant due to its operational simplicity, convenient execution, scalability, tolerance various functional groups.

Language: Английский

Citations

0