Metal-free Lewis-acid-catalyzed divergent trifluoromethylselenolation of alkynes: construction of α-trifluoromethylselenolated ketones and alkynes

Gao, Yan; Xiao, R.; Feng, Bo; Bian, Zhaoying; Zhang, Han; Zhu, Gangguo; Wang, Yanan; Yuan, Zheliang

doi:10.1039/d3qo01111a

Org. Chem. Front.

2023

DOI: 10.1039/d3qo01111a

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Metal-free Lewis-acid-catalyzed divergent trifluoromethylselenolation of alkynes: construction of α-trifluoromethylselenolated ketones and alkynes

Yan Gao¹,

R. Xiao²,

Bo Feng³

et al.

Abstract: Herein, we have developed a mild and efficient Lewis acid-catalyzed divergent trifluoromethylselenolation of alkynes. With trifluoromethyl selenoxide as the electrophilic trifluoromethylselenolation reagent, the terminal and internal aliphatic alkynes could be...

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2024

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Cited by 3 publications

References 83 publications

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Synthesis of Trifluoromethylselenolated Spiro[5.5]trienones/Spiro[4.5]trienones via Electrophilic Trifluoromethylselenolation Cyclization and Dearomatization

Wang,

Niu,

Geng

et al. 2024

Adv Synth Catal

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An expedient strategy for the construction of trifluoromethylselenolated spiro[5.5]trienones/spiro[4.5]trienones through a cascade electrophilic trifluoromethylselenolation cyclization and dearomatization has been developed. This sequential process was induced by N‐trifluoromethylselenophthalimide (Phth‐SeCF3), which was an efficient electrophilic trifluoromethylselenolation reagent. This approach has the feature of mild conditions, broad substrate scope, and high functional group tolerance.

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Synthesis of Trifluoromethylselenolated Spiro[5.5]trienones/Spiro[4.5]trienones via Electrophilic Trifluoromethylselenolation Cyclization and Dearomatization

Wang,

Niu,

Geng

et al. 2024

Adv Synth Catal

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Copper‐Mediated Decarboxylative Trifluoromethylselenolation of Alkynyl Carboxylic Acids with [Me₄N][SeCF₃]

Ding,

Yao,

et al. 2024

Eur J Org Chem

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The synthesis of alkynyl trifluoromethyl selenoethers from copper‐mediated aerobic decarboxylative trifluoromethylselenolation of alkynyl carboxylic acids with [Me4N][SeCF3] is reported. The reaction proceeded smoothly under mild conditions and enabled the facile conversion of both aryl and alkyl alkynyl carboxylic acids to the corresponding trifluoromethyl selenoethers in good yields, demonstrating that decarboxylative trifluoromethylselenolation of alkynyl carboxylic acids with the nucleophilic [Me4N][SeCF3] reagent is feasible at ambient temperature without irradiation. Advantages of the method include the use of bench‐stable and non‐volatile alkynyl carboxylic acids as starting materials, readily accessible SeCF3 reagent, excellent functional group tolerance, and the avoidance of harsh reaction conditions. This copper‐mediated reaction represents the first decarboxylative trifluoromethylselenolation of alkynyl carboxylic acids with a SeCF3 source.

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Progress in Photocatalyzed Trifluoromethylthiolation and Trifluoromethylselenolation Reactions

Li,

Song,

Zhang

et al. 2024

Synthesis

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Photoredox catalysis has evolved into a widely used method and has fostered the extensive utilization of radical coupling partners in organic synthesis over the past years. The integration of visible-light photocatalysis into fluorine chemistry has achieved many important transformations for radical fluorination and fluoroalkylation, which usually proceeded smoothly under mild conditions with simple oxidants or reductants, exhibiting a broad range of substrates and excellent functional group tolerance. In this review, we highlight the photoredox-catalyzed procedures for the trifluoromethylthiolation and trifluoromethylselenolation reactions as well as their possible mechanisms. The ease and environment-friendliness of shuttling electrons back and forth to substrates or intermediates, and selectively transferring energy through visible-light-absorbing catalysts or EDA complexes holds promise to improve the trifluoromethylthiolation and trifluoromethylselenolation in radical chemistry.

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Metal-free Lewis-acid-catalyzed divergent trifluoromethylselenolation of alkynes: construction of α-trifluoromethylselenolated ketones and alkynes

Abstract: Herein, we have developed a mild and efficient Lewis acid-catalyzed divergent trifluoromethylselenolation of alkynes. With trifluoromethyl selenoxide as the electrophilic trifluoromethylselenolation reagent, the terminal and internal aliphatic alkynes could be...

Cited by 3 publications

References 83 publications

Synthesis of Trifluoromethylselenolated Spiro[5.5]trienones/Spiro[4.5]trienones via Electrophilic Trifluoromethylselenolation Cyclization and Dearomatization

Synthesis of Trifluoromethylselenolated Spiro[5.5]trienones/Spiro[4.5]trienones via Electrophilic Trifluoromethylselenolation Cyclization and Dearomatization

Copper‐Mediated Decarboxylative Trifluoromethylselenolation of Alkynyl Carboxylic Acids with [Me₄N][SeCF₃]

Progress in Photocatalyzed Trifluoromethylthiolation and Trifluoromethylselenolation Reactions

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Metal-free Lewis-acid-catalyzed divergent trifluoromethylselenolation of alkynes: construction of α-trifluoromethylselenolated ketones and alkynes

Abstract: Herein, we have developed a mild and efficient Lewis acid-catalyzed divergent trifluoromethylselenolation of alkynes. With trifluoromethyl selenoxide as the electrophilic trifluoromethylselenolation reagent, the terminal and internal aliphatic alkynes could be...

Cited by 3 publications

References 83 publications

Synthesis of Trifluoromethylselenolated Spiro[5.5]trienones/Spiro[4.5]trienones via Electrophilic Trifluoromethylselenolation Cyclization and Dearomatization

Synthesis of Trifluoromethylselenolated Spiro[5.5]trienones/Spiro[4.5]trienones via Electrophilic Trifluoromethylselenolation Cyclization and Dearomatization

Copper‐Mediated Decarboxylative Trifluoromethylselenolation of Alkynyl Carboxylic Acids with [Me4N][SeCF3]

Progress in Photocatalyzed Trifluoromethylthiolation and Trifluoromethylselenolation Reactions

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Copper‐Mediated Decarboxylative Trifluoromethylselenolation of Alkynyl Carboxylic Acids with [Me₄N][SeCF₃]