Recent advances in trifluoroethylation reaction

Zhou, Ming-Xi; Han, Shuai; Wang, Yue; Zhang, Wei; Wang, Zhen; Zeng, Yao-Fu

doi:10.1039/d3qo01366a

Org. Chem. Front.

2023

DOI: 10.1039/d3qo01366a

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Recent advances in trifluoroethylation reaction

Ming-Xi Zhou,

Shuai Han,

Yue Wang

et al.

Abstract: Trifluoroethyl group served as the bioisosteres of ethyl or ethoxy group widely exists in the fields of pharmaceuticals and agrochemicals. Developing novel strategies of introducing trifluoroethyl group into various skeletons...

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2024

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Cited by 5 publications

(2 citation statements)

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“…insertion reactions. 8 Due to a strong driving force for βfluoride elimination, the flourishing metal-carbene-mediated protocols are unsuited for the difunctionalization of CF 3 CHN 2 . 9 There are several successful examples based on diazonium ion intermediates (Scheme 1b).…”

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confidence: 99%

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Visible-Light-Promoted Radical gem-Selenosulfonylation or -Iodosulfonylation of 2,2,2-Trifluorodiazoethane under Photosensitizer-Free Conditions

Li,

Ling,

Zhou

2024

Org. Lett.

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mentioning

confidence: 99%

“…It has also been employed as a new type of trifluoroethyl agent in various X–H (X = C, N, O, S, P, etc.) insertion reactions . Due to a strong driving force for β-fluoride elimination, the flourishing metal-carbene-mediated protocols are unsuited for the difunctionalization of CF 3 CHN 2 .…”

mentioning

confidence: 99%

Visible-Light-Promoted Radical gem-Selenosulfonylation or -Iodosulfonylation of 2,2,2-Trifluorodiazoethane under Photosensitizer-Free Conditions

Li,

Ling,

Zhou

2024

Org. Lett.

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TBHP‐Mediated Hydroxyperfluoroalkylation of Alkenes with Perfluoroalkyl Iodides to Construct β‐Perfluoroalkyl Alcohols

Zhang,

Zhu,

et al. 2024

Adv Synth Catal

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A three‐component strategy for the synthesis of β‐perfluoroalkyl allyl alcohols from 1,3‐dienes is developed. A diverse range of synthetically valuable β‐perfluoroalkyl allyl alcohols are obtained in moderate to high yields. Broad substrate scope and good functional group tolerance are observed. This method is also applicable to mono‐olefins and 1,3‐enynes. The control experiment results demonstrate that the hydroxyl group OH in the product comes from TBHP. In addition, the practicality and mild reaction conditions make these synthetic transformations attractive and valuable for organic synthesis.

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Three‐Component Reactions of Alkenes with C−C Bond Formation: Recent Developments

Wang,

Li,

et al. 2024

Eur J Org Chem

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Alkenes are highly valuable materials in organic synthesis, and their three‐component reactions offer a promising method for C‐C bond formation and carbon chain elongation. This approach not only reduces the number of reaction steps but also minimizes waste generation, enabling the preparation of polysubstituted alkanes from simple starting materials. In this review, we provide an overview of recent advancements in this field from 2013 to 2023. We have classified the developments into three main categories: (1) reactions triggered by C‐radicals or heteroatom‐radicals; (2) cascades involving three‐membered ring intermediates; and (3) transformations catalyzed by metals. We will discuss a wide range of reactions that involve diazoium salts, arylhydrazines, acids, aldehydes, 1,3‐dicarbonyls, diazo compounds, amines, malononitriles, diacyl peroxides, ethers, 1,3‐dithiane, arenes, CuSCF3, selectfluor, Et3N•3HF, TBHP, CH2Cl2, CHCl3, CO2, CO, KCl, H2O, and other reagents. These reactions lead to alkylation, arylation, or carbonylation products. We believe that this review will be helpful for future research in this area.

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Recent advances in trifluoroethylation reaction

Abstract: Trifluoroethyl group served as the bioisosteres of ethyl or ethoxy group widely exists in the fields of pharmaceuticals and agrochemicals. Developing novel strategies of introducing trifluoroethyl group into various skeletons...

Cited by 5 publications

References 125 publications

Visible-Light-Promoted Radical gem-Selenosulfonylation or -Iodosulfonylation of 2,2,2-Trifluorodiazoethane under Photosensitizer-Free Conditions

Visible-Light-Promoted Radical gem-Selenosulfonylation or -Iodosulfonylation of 2,2,2-Trifluorodiazoethane under Photosensitizer-Free Conditions

TBHP‐Mediated Hydroxyperfluoroalkylation of Alkenes with Perfluoroalkyl Iodides to Construct β‐Perfluoroalkyl Alcohols

Three‐Component Reactions of Alkenes with C−C Bond Formation: Recent Developments

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