Regioselective Synthesis of Thiazole‐5‐thione Based on [2 + 3] Annulation Trapping of α‐Keto Sulfine with Thioamide DOI
Xuehua Zhang, Yong Lin, Mingyang Guo

et al.

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

Published: Oct. 22, 2024

Abstract Aiming to develop novel annulation reactions using sulfine intermediates, we have established a regioselective formal [2+3] cyclization reaction of α ‐keto sulfines generated from the elimination arylacyl sulfoxides and thioamides. This new strategy allows for synthesis thiazole‐5‐thiones directly without catalysts or additives. The approach features step‐economic, one‐pot characteristics via tandem sequence in situ generation, regiospecifically nucleophilic attack [3+2] cyclizatoin, dithioate (S=C−S−) skeletons formation, subsequent intramolecular cyclization. also represents method constructing skeletons.

Language: Английский

Boosting N-Heterocyclic Carbene Radical Organocatalysis with Nickel Chemistry: A Rational Mechanistic Study-Based Approach DOI
Ludivine Delfau,

Elena Mauro,

Jacques Pécaut

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(9), P. 7149 - 7156

Published: April 23, 2024

A cooperative NHC/nickel catalytic methodology has been developed for the synthesis of ketones employing aromatic aldehydes and tertiary alkyl iodides. All key steps postulated cycle were validated with comprehensive stoichiometric electrochemical studies, including reduction NiII by deprotonated Breslow intermediate, Ni0 promoted halogen-atom abstraction to generate transient radicals, coupling between latter persistent acyl thiazolium radical intermediate. Such a broadly proposed accepted, yet elusive, intermediate isolated studied single-crystal X-ray diffraction study.

Language: Английский

Citations

2
Regioselective Synthesis of Thiazole‐5‐thione Based on [2 + 3] Annulation Trapping of α‐Keto Sulfine with Thioamide DOI
Xuehua Zhang, Yong Lin, Mingyang Guo

et al.

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

Published: Oct. 22, 2024

Abstract Aiming to develop novel annulation reactions using sulfine intermediates, we have established a regioselective formal [2+3] cyclization reaction of α ‐keto sulfines generated from the elimination arylacyl sulfoxides and thioamides. This new strategy allows for synthesis thiazole‐5‐thiones directly without catalysts or additives. The approach features step‐economic, one‐pot characteristics via tandem sequence in situ generation, regiospecifically nucleophilic attack [3+2] cyclizatoin, dithioate (S=C−S−) skeletons formation, subsequent intramolecular cyclization. also represents method constructing skeletons.

Language: Английский

Citations

0