Synthesis of naphtho[1,2-b]furan-2-carbaldehydes and naphtho[2,1-b]furan-2-carbaldehydes via electrocatalytic 3,3-rearrangement/cyclization of propargylic aryl ethers under mild conditions DOI Creative Commons

Kaili Cen,

Mixia Ouyang,

Guojun He

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: June 1, 2024

An electrocatalytic 3,3-rearrangement/cyclization approach has been developed for the transformation of aryl-substituted propargylic aryl ethers to naphtho[1,2-b]furan-2-carbaldehyde and naphtho[2,1-b]furan-2-carbaldehyde derivatives. The reaction proceeded efficiently under mild conditions in absence metal- chemical-oxidant, yielding desired products with good substrate scope functional group tolerance via a radical pathway. Furthermore, control experiment revealed that phenylselenyl-substituted secondary alcohol might be intermediate, 18O labeling indicated oxygen source product possibly deriving from water. Significantly, further transformations were conducted showcase utility this electrosynthesis strategy.

Language: Английский

Reactions of alkynes with C–S bond formation: recent developments DOI

Yuemei Xu,

S. ZHANG, Dayun Huang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(32), P. 6443 - 6484

Published: Jan. 1, 2024

Alkynes are important in organic synthesis. This review mainly focuses on the recent advances (2013–2023) alkynes with C–S bond formation, based more than 30 kinds of sulfur reagents.

Language: Английский

Citations

2

Electrochemically promoted selenocyclization for the synthesis of organoselenyl isoxazoles DOI
Nan Sun, Zhi Qiao,

Jiamin Li

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(19), P. 10240 - 10246

Published: Jan. 1, 2024

Herein, we report a general and sustainable electrochemically promoted oxidative selenocyclization protocol for the synthesis of organoselenyl isoxazoles from 2-alkyn-1-one O -methyloximes diorganyl diselenides.

Language: Английский

Citations

2

Visible-Light-Induced Stereoselective Radical trans-Iodoalkylation of Terminal Alkyne with Iodoform DOI
Shaoqun Zhu,

Lizi Jia,

Qi Cheng

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(39), P. 8400 - 8404

Published: Sept. 25, 2024

We describe herein a novel stereoselective

Language: Английский

Citations

2

Thiocyanoalkylation of Alkenes via Dual Photoredox and Copper Catalysis DOI
Xu Wang,

Bi-Yin Xiao,

Qin Jiang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 7, 2024

Organic thiocyanates are commonly used as essential organic synthesis intermediates and widely present in various drug molecules bioactive molecules.

Language: Английский

Citations

2

Electrochemical oxidative heterodifunctionalization of dehydroalanine: access to unnatural α,α-disubstituted amino esters DOI
Hui Cao, Ruitao Wang,

Qianqiu Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2566 - 2571

Published: Jan. 1, 2024

A general, efficient, and mild Dha electrochemical modification strategy is reported, which enables a divergent route to various α,α-disubstituted amino esters via anodic cascade oxidation nucleophilic attack.

Language: Английский

Citations

1

NBS-Promoted Synthesis of Thiocyanated Aminomaleimides and Site-Selective Intramolecular Cyclization Access to 1,4-Benzothiazepines via S–CN Bond Cleavage DOI
Qi Yang,

Shuntao Huang,

Lu Yin

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(8), P. 5266 - 5276

Published: April 9, 2024

A transition metal-free concise and efficient protocol for the synthesis of thiocyanated aminomaleimides benzo[e][1,4]thiazepine derivatives has been developed. The method involves an initial α-C–H thiocyanation with KSCN TEMPO-mediated tandem S–CN bond cleavage/intramolecular cyclization substitution processes, which enables formation seven-membered S/N-heterocycles. This synthetic strategy provides a reliable biologically interesting by using as sulfur sources well expands application enaminones reactions in heterocycles synthesis.

Language: Английский

Citations

1

Electrochemical Oxidative Cross-Coupling Reactions of Ketene Dithioacetals and Dichalcogenides to Construct C−Se/C−S Bonds DOI Creative Commons
Jiaxu Wang, Xin Liu,

Chenglong Feng

et al.

Journal of The Electrochemical Society, Journal Year: 2024, Volume and Issue: 171(5), P. 055501 - 055501

Published: April 19, 2024

A green protocol for construction of C−Se bonds from ketene dithioacetals and diselenides through direct electrochemical oxidative cross-coupling has been developed. This reaction was carried out in an undivided cell system with NaBF 4 as the electrolyte CH 3 CN solvent galvanostatic electrolysis. series substituted were tolerant desired tetrasubstituted alkenyl selenides obtained moderate to excellent yields. In addition, C−S bond disulfides method presence KI also successfully realized. It exhibited high efficiency broad functional group tolerance.

Language: Английский

Citations

1

Organoboron-Promoted Electrochemical Chlorosulfonylation of Alkenes with Sulfonyl Chlorides DOI
Xi Peng,

Shaokun Tao,

Weichao Xue

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 4018 - 4023

Published: April 26, 2024

Although extraordinary advances have been achieved by the transition-metal catalysis system, there is an urgent need to explore and develop alternative methodologies that are more environmentally friendly. Herein, we report electrochemical chlorosulfonylation of alkenes using a wide range sulfonyl chlorides with inexpensive, degradable, commercially available organoboron as promoter. Furthermore, this protocol employs convergent paired electrolysis, reducing for sacrificial anodes minimizing extent hydrogen evolution.

Language: Английский

Citations

1

Electrochemically Benzyl Cation‐Triggered Alkylacetoxylation of Terminal Alkynes and Carboxylic Acids DOI
Na Yang, Hui Gao,

Peng‐Zhan Zhang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(12), P. 2721 - 2727

Published: May 11, 2024

Abstract A catalyst‐free electrochemical alkylacetoxylation reaction of terminal alkynes with (thio)xanthenes and carboxylic acids is developed. Treating the addition products K 2 CO 3 as a base in methanol affords ketones moderate to good yields. Preliminary experimental computational studies indicate that benzylic cation generated from triggers electrophilic alkynes.

Language: Английский

Citations

1

Recent Developments in Selenylation of Alkynes DOI

Yuemei Xu,

Dayun Huang,

Jinjing Wu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: July 29, 2024

Abstract Alkynes are simple yet important organic feedstocks. The selenylation of alkynes is able to produce complex selenium‐containing compounds in a facile way. Although there some reviews about the alkynes, most them focus on one specific reaction or what types products that can be obtained. There lack attention given various uses different selenium reagents and their mechanisms. This review mainly focuses recent advances (2013–2023) based diverse reagents. Mechanisms how added work will discussed. Different types, including difunctionalization, Se‐annulation, spiro‐cyclization, C−Se coupling, click recorded this review. regioselectivity achieved through mechanisms, radicals, seleniraniums electrophilic cyclization. We hope it do help for future research area.

Language: Английский

Citations

1