Nickel-Catalyzed Multicomponent Assembly of Alkynes toward α-CF3-Alkenes DOI
Ling Li,

Yingmei Li,

Chongchong Yan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(26), P. 5566 - 5570

Published: June 21, 2024

We disclose an efficient nickel catalytic system for expediting the coupling of alkynes with fluoroalkyl hydrazones and boronic acids, thus facilitating synthesis stereospecific α-fluoroalkyl-alkene derivatives. 3H-Pyrazoles might be involved as key intermediates through a nitrogen-releasing process, enabling subsequent acids to afford 1,2-difunctional alkenes in highly step-economical fashion. This tandem platform demonstrates broad functional group tolerance, including complex natural products drug-like molecules.

Language: Английский

The Carbene Chemistry of N-Sulfonyl Hydrazones: The Past, Present, and Future DOI
Xiaolong Zhang, Paramasivam Sivaguru,

Yongzhen Pan

et al.

Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 10, 2025

N-Sulfonyl hydrazones have been extensively used as operationally safe carbene precursors in modern organic synthesis due to their ready availability, facile functionalization, and environmental benignity. Over the past two decades, there has tremendous progress chemistry of N-sulfonyl presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Many transfer reactions are unique cannot be achieved by any alternative methods. The discovery novel development highly enantioselective new skeletal editing represent notable recent achievements hydrazones. This review describes overall made hydrazones, organized based on reaction types, spotlighting current state-of-the-art remaining challenges addressed future. Special emphasis is devoted identifying, describing, comparing scope limitations methodologies, key mechanistic scenarios, potential applications complex molecules.

Language: Английский

Citations

6
Who is Who in the Carbene Chemistry of N‐Sulfonyl Hydrazones DOI
Paramasivam Sivaguru,

Yongzhen Pan,

Nan Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(17), P. 2071 - 2108

Published: May 27, 2024

Comprehensive Summary Over the past few decades, N ‐sulfonyl hydrazones have been recognized as alternative precursors for hazardous diazo compounds in organic synthesis, allowing diverse innovative and original chemical transformations that were otherwise difficult to achieve. This critical review summarizes major advancements carbene chemistry of hydrazones. The contents this are organized based on research conducted by leading scientists who made significant contributions field. individual transfer reactions their mechanisms, well potential applications synthesis natural products complex bioactive molecules, thoroughly discussed.

Language: Английский

Citations

8
Transition‐Metal‐Catalyzed Reactions Involving Trifluoro Diazo Compounds and Their Surrogates DOI
Yeming Wang, Chaoqun Zhang,

Shizhe Li

et al.

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

Published: May 22, 2024

Abstract Fluorinated organic compounds represent an important and growing family of active ingredients in various fields, including material science, pharmaceutical chemistry biological science. Developing efficient synthetic methods toward fluorinated have attracted much attention. In recent years, transition‐metal catalyzed reaction trifluoro diazo were a powerful convenient approach to afford trifluoromethyl‐ difluoromethyl‐substituted value. this review, the progress on transition‐metal‐catalyzed reactions involving their surrogates via trifluoromethylated carbene complex is described sequence 2,2,2‐trifluorodiazoethane as precursor, ethyl 3‐trifluoro‐2‐diazo‐propionate trifluoroethylamine hydrochloride or amines CF 3 CHN 2 surrogate well aldehydes/ketones N‐sulfonylhydrazones surrogate.

Language: Английский

Citations

3
Expedient Synthesis of gem-CF2-2H-Thiophenes from Enaminothiones DOI
Zhengyu Zhang, Yaojia Jiang, Xinyu Zhang

et al.

Synlett, Journal Year: 2024, Volume and Issue: 35(18), P. 2113 - 2116

Published: April 8, 2024

Abstract An expedient and easy-to-handle synthetic platform has been established for the constructing of 2H-thiophenes carrying fluorine atoms through [4+1] cyclization enaminothiones with fluorinated carbene precursors. This simple reaction system is well compatible a wide range substrates under completely metal-free conditions. The resulting can undergo further late-stage modifications to yield fluorine-substituted heterocycles.

Language: Английский

Citations

0
Nickel-Catalyzed Multicomponent Assembly of Alkynes toward α-CF3-Alkenes DOI
Ling Li,

Yingmei Li,

Chongchong Yan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(26), P. 5566 - 5570

Published: June 21, 2024

We disclose an efficient nickel catalytic system for expediting the coupling of alkynes with fluoroalkyl hydrazones and boronic acids, thus facilitating synthesis stereospecific α-fluoroalkyl-alkene derivatives. 3H-Pyrazoles might be involved as key intermediates through a nitrogen-releasing process, enabling subsequent acids to afford 1,2-difunctional alkenes in highly step-economical fashion. This tandem platform demonstrates broad functional group tolerance, including complex natural products drug-like molecules.

Language: Английский

Citations

0