Copper-Catalyzed One-Step Formation of Four C–N Bonds toward Polyfunctionalized Triazoles via Multicomponent Reaction DOI

Xuelun Duan,

Nan Zheng,

Gongbo Liu

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(32), P. 6006 - 6012

Published: Aug. 5, 2022

A novel four-component reaction of alkynes, amines, azides, and 2H-azirines has been developed for the first time by efficient formation four C–N bonds in one step under mild conditions, rapidly preparing polyfunctionalized triazoles with molecular diversity involving three different intermediates copper–acetylide, copper–allenylidene, copper–vinyl nitrene. Propargylic ester is disclosed as a "three-in-one" building block possessing triplicate cycloaddition nucleophilic electrophilic properties, which could enable such transformation high yields, broad substrate scope, functionalization.

Language: Английский

Electrochemical stereoselective synthesis of polysubstituted 1,4-dicarbonyl Z-alkenes via three-component coupling of sulfoxonium ylides and alkynes with water DOI Creative Commons

Haoran Li,

Y. Ran,

Yu-Yi Zhu

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(21), P. 8156 - 8162

Published: Jan. 1, 2024

The first straightforward strategy for the synthesis of 1,4-dicarbonyl Z-alkenes has been developed via an electrochemical cross-coupling reaction sulfoxonium ylides and alkynes with water. metal-free protocol showed easy-to-handle nature, good functional group tolerance, high Z-stereoselectivity, which is rare in previous cases. proposed mechanism was convincingly established by carrying out a series control experiments, cyclic voltammetry density theory (DFT) studies.

Language: Английский

Citations

3

α-(N-Alkyl-N-heteroarenium)-α-diazoacetates: synthesis and reactivity of a novel class of ‘onium’ diazo compounds DOI
Yaxi Li,

Quan-Yun Liu,

Yi Zhang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Unprecedented diazoacetate N -heteroarenium salts are synthesized and participate in catalytic [2 + 1] cycloadditions [2,3]-sigmatropic rearrangements, providing facile access to otherwise difficult-to-obtain multi-functionalized -heterocycles.

Language: Английский

Citations

3

Ru-Catalyzed Hydrogen Atom Transfer/C–F Bond Cleavage of Difluoroalkyl Diazos with Hantzsch Ester via a Photocatalytic Radical Process DOI
Qian Wang, Jiang Liu, Haibo Mei

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(43), P. 8036 - 8040

Published: Oct. 26, 2022

A Ru-catalyzed reaction of difluoroalkyl diazo compounds with Hantzsch ester under visible light to achieve the formation α-fluorovinylphosphonates via a radical process has been developed. Mechanistic experiments and density functional theory calculations reveal that generation carbon is directly through hydrogen atom transfer (HAT) by ester. This system represents first example radicals from Hantzsch-ester-assisted HAT also demonstrates new radical-involved pathway for compounds.

Language: Английский

Citations

14

Visible light photoredox-catalyzed deoxydisulfuration of alcohols DOI
Chaoyang Liu,

Xiaoman Lin,

Delie An

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(2), P. 358 - 363

Published: Nov. 22, 2023

Herein, we present a versatile approach for the photoredox-catalyzed deoxydisulfuration of primary, secondary, and tertiary alcohols, utilizing tetrasulfides to facilitate efficient synthesis unsymmetrical disulfides.

Language: Английский

Citations

8

Copper-Catalyzed One-Step Formation of Four C–N Bonds toward Polyfunctionalized Triazoles via Multicomponent Reaction DOI

Xuelun Duan,

Nan Zheng,

Gongbo Liu

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(32), P. 6006 - 6012

Published: Aug. 5, 2022

A novel four-component reaction of alkynes, amines, azides, and 2H-azirines has been developed for the first time by efficient formation four C–N bonds in one step under mild conditions, rapidly preparing polyfunctionalized triazoles with molecular diversity involving three different intermediates copper–acetylide, copper–allenylidene, copper–vinyl nitrene. Propargylic ester is disclosed as a "three-in-one" building block possessing triplicate cycloaddition nucleophilic electrophilic properties, which could enable such transformation high yields, broad substrate scope, functionalization.

Language: Английский

Citations

13