Yinxia Cai

Shanghai Institute of Technology

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Caiyun Ou

Shanghai Institute of Technology

Chao Liu

Shanghai Institute of Organic Chemistry

Yuyang Ma

China Railway 18th Bureau Group Corporation

Xiaoyu Ma

Second Hospital of Shandong University

Lingling Shan

Soochow University

Zhanhu Ma

Shanghai Institute of Technology

Yong Guo

Shanghai Institute of Organic Chemistry

Qijun Pan

Shanghai Institute of Technology

Haozhen Zhang

Shanghai Institute of Technology

Chao Liu

Chinese Academy of Sciences

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Shanghai Institute of Technology

Shanghai Institute of Organic Chemistry

State Key Laboratory of Pollution Control and Resource Reuse

Henan University

University of Chinese Academy of Sciences

Chinese Academy of Sciences

Lanzhou Institute of Chemical Physics

Guizhou University

Jingdong (China)

Soochow University

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Visible-Light-Mediated Trifluoromethylalkynylation of Unactivated 1,6-Dialkenes

Chinese Journal of Organic Chemistry (2023)

Yinxia Cai Chao Liu

Plausible reaction mechanism

10.6023/cjoc202300058

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Aryl sulfonyl fluoride synthesisviapalladium-catalyzed fluorosulfonylation of aryl thianthrenium salts

Organic & Biomolecular Chemistry (2023)

Lingling Shan Zhanhu Ma Caiyun Ou Yinxia Cai Yuyang Ma

We developed an efficient palladium-catalyzed fluorosulfonylation reaction of aryl thianthrenium salts to smoothly prepare various aryl sulfonyl fluorides using cheap Na2S2O4 as a convenient sulfonyl source in combination with N-fluorobenzenesulfonimide (NFSI) as an ideal fluorine source under mild reduction conditions. A one-pot synthesis of aryl sulfonyl fluorides starting from various arenes was established as well without the need for separating aryl thianthrenium salts. The practicality of this protocol was demonstrated by gram-scale synthesis, derivatization reactions, and excellent yields.

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Fluorine

10.1039/d3ob00462g

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Aryl sulfonyl fluoride synthesis via organophotocatalytic fluorosulfonylation of diaryliodonium salts

Organic & Biomolecular Chemistry (2023)

Yuyang Ma Qijun Pan Caiyun Ou Yinxia Cai Xiaoyu Ma

An efficient metal-free visible-light-mediated protocol for the synthesis of various aryl sulfonyl fluorides from diaryliodonium salts via a radical sulfur dioxide insertion and fluorination strategy was developed.

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Fluorine

10.1039/d3ob01200j

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Sulfonyl fluoride synthesis via visible-light-mediated fluorosulfonylation of thianthrenium salts

Synthetic Communications (2023)

Lingling Shan Zhanhu Ma Caiyun Ou Yinxia Cai Yuyang Ma

AbstractA visible-light-mediated fluorosulfonylation reaction of thianthrenium salts has been developed to prepare various sulfonyl fluorides with 1,4-diazabicyclo [2.2.2] octane bis (sulfur dioxide) (DABSO) as sulfonyl source and cheap KHF2 as fluorine source based on radical sulfur dioxide insertion and fluorination strategy. This operationally simple protocol proceeds with high functional-group tolerance under mild reaction conditions.Keywords: Fluorosulfonylationthianthrenium saltsvisible-light-mediated Disclosure statementNo potential conflict of interest was reported by the author(s).Additional informationFundingThe authors gratefully acknowledge the financial support from the National Natural Science Foundation of China [No. 21871283], the project of Science and Technology Commission of Shanghai Municipality in China [21010503800], Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai Engineering Research Center of Green Fluoropharmaceutical Technology, and the Science Research Foundation of Shanghai Institute of Technology.

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10.1080/00397911.2023.2246603

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Aliphatic Sulfonyl Fluoride Synthesis via Decarboxylative Fluorosulfonylation of Hypervalent Iodine(III) Carboxylates

Organic Letters (2023)

Caiyun Ou Yinxia Cai Yuyang Ma Haozhen Zhang Xiaoyu Ma

We disclose herein a photocatalytic decarboxylative fluorosulfonylation reaction of various hypervalent iodine(III) carboxylates in combination with 1,4-diazabicyclo[2.2.2]octane–bis(sulfur dioxide) adduct as a sulfonyl source and KHF2 as a desirable fluorine source via a radical sulfur dioxide insertion and fluorination strategy. A one-pot photocatalytic decarboxylative fluorosulfonylation reaction of various carboxylic acids mediated by PhI(OAc)2 was realized, as well. Notably, this transformation can be performed under heating conditions without the need for catalysts.

Hypervalent molecule

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Fluorine

10.1021/acs.orglett.3c02652

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Citations (14)