Light-Induced Reactivity of Nucleophilic Siloxycarbene with Heterocumulenes: Synthesis of α-Ketoamides, Hydantoins, Oxoacetamidines, and Amides DOI
Mohammad Saleem,

Pandey Abhishek,

Dongari Yadagiri

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 25, 2024

We report the reactivity of in situ-generated nucleophilic siloxycarbenes from acylsilanes via 1,2-Brook rearrangement presence visible light with heterocumulenes. This method significantly advances conventional use electrophilic carbenes stabilized by metal catalysts and harsh reaction conditions. The was explored isocyanates, carbodiimides,

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

2
Electrophilic Halogenation of Allenoates and 3-Alkynoates: Synthesis of 1,4-Dicarbonyl (E)-3-Haloalkenes and Mechanistic Investigations DOI
Paru Jamwal, Yumnam Nganthoinganbi, Ming‐Kang Tsai

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 26, 2025

Allenoates traditionally provide halobutenolides upon reaction with halonium ions via electrophile-assisted halolactonization. Herein, an unusual electrophilic halogenation of di- and trisubstituted allenoates 3-alkynoates is demonstrated N-halosuccinimides under DABCO promotion. The protocol affords densely functionalized 1,4-dicarbonyl 3-haloalkenes in good yields excellent (E)-stereoselectivity (up to 83% yield, >20:1 dr). are presumed form γ-haloallenoate intermediates, which further react the desired scaffolds. role nucleophilic base transformation demystified through control experiments computational studies. deliverables identified as synthons for various synthetic group transformations valuable targets biologically active pyridazine

Language: Английский

Citations

0
Photoactivation of Hydrazones for the Synthesis of Diarylalkanes and Trialkylmethylboronates: The Key Role Played by Soluble Base DOI
Po-Kai Peng, Clayton P. Donald,

Zhencheng Dong

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(16), P. 3397 - 3400

Published: April 11, 2024

The synthesis of diaryl alkanes and tertiary organoboronates via Barluenga coupling at room temperature occurred photoactivated conversion aryl sulfonyl hydrazones to diazo compounds in the presence soluble bases. combination arylsulfonyl hydrazone a base is necessary provide near-UV chromophore. Using aromatic boronic acids resulted rapid deboronation because instability dibenzylic boron intermediates. Alkyl allowed isolation derivatives boronate.

Language: Английский

Citations

3
Light-Driven Intramolecular Cyclopropanation of Alkene-Tethered N-Tosylhydrazones: Synthesis of Fused-Cyclopropane γ-Lactones DOI
Pokhriyal Yamini, Akanksha Babbar, Dongari Yadagiri

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(28), P. 6035 - 6040

Published: July 10, 2024

Fused-cyclopropane ring-containing γ-lactone compounds are versatile building blocks in many fields, including the synthesis of biologically active compounds. Here, we report light-driven intramolecular cyclopropanation alkene-tethered

Language: Английский

Citations

2
Transition-metal-free synthesis of triarylmethanes via Friedel-Crafts reactions of imidazo[1,2-a]pyridines with chlorohydrocarbon derivatives DOI Creative Commons

Xinlei Fu,

Longhui Wu,

Xiaohua Guo

et al.

Journal of Saudi Chemical Society, Journal Year: 2024, Volume and Issue: 28(4), P. 101883 - 101883

Published: May 29, 2024

A facile, transition-metal-free, HFIP-promoted method for the synthesis of triarylmethanes through direct Friedel-Crafts reactions imidazo[1,2-a]pyridines with chlorohydrocarbon derivatives has been described, which allows efficient containing in good to satisfactory yields at room temperature. This transformation features simple operation, excellent functional group tolerance, and a broad substrate scope.

Language: Английский

Citations

0
Light-Induced Reactivity of Nucleophilic Siloxycarbene with Heterocumulenes: Synthesis of α-Ketoamides, Hydantoins, Oxoacetamidines, and Amides DOI
Mohammad Saleem,

Pandey Abhishek,

Dongari Yadagiri

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 25, 2024

We report the reactivity of in situ-generated nucleophilic siloxycarbenes from acylsilanes via 1,2-Brook rearrangement presence visible light with heterocumulenes. This method significantly advances conventional use electrophilic carbenes stabilized by metal catalysts and harsh reaction conditions. The was explored isocyanates, carbodiimides,

Language: Английский

Citations

0