Electrochemical α-C(sp3)–H/N–H Cross-Coupling of Isochromans and Azoles DOI Creative Commons
Guoping Li, Bing Yan, Liangliang Wu

et al.

Molecules, Journal Year: 2024, Volume and Issue: 30(1), P. 4 - 4

Published: Dec. 24, 2024

Isochroman and azole moieties are both present in a wide variety of biologically active molecules. Their efficient combination under mild reaction conditions is beneficial for obtaining small-molecule drug candidates. In this paper, we describe electrochemical α-C(sp3)–H/N–H cross-coupling reactions between isochromans azoles, yielding products moderate to excellent yields. This protocol does not require any catalysts or exogenous oxidants can be performed at room temperature air. Control experiments cyclic voltammetry showed that the may proceed through radical coupling nucleophilic addition processes.

Language: Английский

Electrochemical N–H Methylsulfoxidation of Sulfoximines with DMSO DOI Open Access

Qing‐Ru Zhu,

Gen Liu, Yongxiang Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 16, 2025

Comprehensive Summary The N–H methylsulfoxidation of sulfoximines using DMSO as a methylsulfinyl source, induced by electrochemistry, has been developed. This method is the first example an electrochemical reaction in which serves source. Unlike previous reactions involving substrate, exclusively proceed via radical mechanisms, this follows S‐cation pathway. A wide range N ‐methylsulfinyl were successfully obtained.

Language: Английский

Citations

0
Electrochemical Strategy for the Radical Fluoroacetylation of Sulfoximines from Fluorinated Alkyl Carboxylic Acids DOI
Xiaoman Li, Jiawei Huang, Huanhuan Song

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 15, 2025

The integration of trifluoroacetyl (CF3CO) groups into organic skeletons is a key research topic in synthetic chemistry given their significant potential to boost biological activity. Despite recent developments strategies for incorporating moiety via radical intermediates, the practical utilization inexpensive and readily available trifluoroacetic acids as sources has not yet been developed. Herein, an electrochemical strategy employed achieve deoxygenative transformation directly with assistance PPh3. obtained radicals are then coupled sulfoximine species, thus enabling synthesis N-trifluoroacetylated sulfoximines. Additionally, other fluorinated alkyl carboxylic acids, including perfluoro-, difluoro-, trifluoromethylcarboxylic can also be efficiently utilized under these conditions, leading corresponding acylated Moreover, trifluoroacetylation drug-based molecules easy execution scale-up experiments highlight applicability this protocol.

Language: Английский

Citations

0
Electrochemical Cyclization of o-Aminyl Azobenzenes: Roles of Aldehydes in N–N Bond Cleavage DOI
Anni Li,

Anna Gao,

K. K. N. CHEN

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6324 - 6329

Published: July 22, 2024

Direct functionalization of azobenzenes provides an approach to obtaining valuable molecules in synthetic chemistry. However, efficient method for the cleavage N═N bond azobenzenes, which is a key process this transformation, still lacking. We herein disclose electrochemical reduction-induced cyclization with aldehydes via cleavage. This proceeds well absence any transition metals or external chemical oxidants, leading formation N-protected benzimidazoles moderate good yields.

Language: Английский

Citations

3
GreenMedChem-Inspired Light-Air Mediated C(sp3)-H Bond Oxidation: A New tool for Isoquinolone Synthesis DOI
Qi Zhang, Wenbing Dai, Da‐Le Guo

et al.

European Journal of Medicinal Chemistry, Journal Year: 2025, Volume and Issue: 288, P. 117414 - 117414

Published: Feb. 19, 2025

Language: Английский

Citations

0
Electrochemical N‐Centered Radical‐Triggered Intramolecular N‐N Coupling for the Cyclization of o‐Aminyl Azobenzenes DOI Open Access

Anna Gao,

K. K. N. CHEN,

Fang Ma

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(46)

Published: Aug. 28, 2024

Abstract An electrochemical radical cyclization of o ‐aminyl azobenzenes via N ‐centered generation has been developed for the synthesis benzotriazoles. The bearing a sulfonyl protection on amine readily proceeds in absence any external transition metal catalyst or chemical oxidant, and exhibits good tolerance towards functional groups.

Language: Английский

Citations

1
Direct N H heteroarylation of NH-sulfoximines under electrochemical conditions DOI
Changsheng Qin, Jingfang Wang,

Fang Gao

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 568, P. 114485 - 114485

Published: Aug. 27, 2024

Language: Английский

Citations

0
Electrochemical α-C(sp3)–H/N–H Cross-Coupling of Isochromans and Azoles DOI Creative Commons
Guoping Li, Bing Yan, Liangliang Wu

et al.

Molecules, Journal Year: 2024, Volume and Issue: 30(1), P. 4 - 4

Published: Dec. 24, 2024

Isochroman and azole moieties are both present in a wide variety of biologically active molecules. Their efficient combination under mild reaction conditions is beneficial for obtaining small-molecule drug candidates. In this paper, we describe electrochemical α-C(sp3)–H/N–H cross-coupling reactions between isochromans azoles, yielding products moderate to excellent yields. This protocol does not require any catalysts or exogenous oxidants can be performed at room temperature air. Control experiments cyclic voltammetry showed that the may proceed through radical coupling nucleophilic addition processes.

Language: Английский

Citations

0