{"title":"氟烷基化策略的最新进展：探索砜基和亚砜基试剂在单、双和三氟甲基化反应中的新型活性和合成应用","authors":"Alexander Knieb, G. K. Surya Prakash","doi":"10.1055/s-0043-1775391","DOIUrl":null,"url":null,"abstract":"<p>Fluoroalkylation serves as a pivotal strategy for chemists to precisely alter the properties of small molecules. Among the established fluoroalkylation protocols, sulfone and sulfinate reagents stand out as versatile tools for these reactions, particularly in mono-, di-, and trifluoromethylations. Their versatility lies in offering multiple pathways, encompassing electrophilic, nucleophilic, as well as radical mechanisms, thus providing diverse routes for controlled molecular modifications through a variety of very exciting mechanistic paths.</p> <p>1 Introduction</p> <p>2 Monofluoromethylation Strategies</p> <p>2.1 Fluorobis(phenylsulfonyl)methane (FBSM)</p> <p>2.2 2-Fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide (FBDT)</p> <p>2.3 Benzothiazole-SO<sub>2</sub>CH<sub>2</sub>F, NaSO<sub>2</sub>CH<sub>2</sub>F, and ClSO<sub>2</sub>CH<sub>2</sub>F</p> <p>2.4 PhSO<sub>2</sub>CH<sub>2</sub>F</p> <p>3 Difluoromethylation Strategies</p> <p>3.1 PhSO<sub>2</sub>CF<sub>2</sub>H</p> <p>3.2 Benzothiazole-SO<sub>2</sub>CF<sub>2</sub>H</p> <p>3.3 2-PyrSO<sub>2</sub>CF<sub>2</sub>H</p> <p>3.4 NaSO<sub>2</sub>CF<sub>2</sub>H</p> <p>4 Trifluoromethylation Strategies</p> <p>4.1 PhSO<sub>2</sub>CF<sub>3</sub>\n</p> <p>4.2 2-PyrSO<sub>2</sub>CF<sub>3</sub>\n</p> <p>4.3 Benzothiazole-SO<sub>2</sub>CF<sub>3</sub>\n</p> <p>4.4 NaSO<sub>2</sub>CF<sub>3</sub>\n</p> <p>4.4.1 Electrochemical Approaches</p> <p>4.4.2 Photochemical Approaches</p> <p>4.4.3 Other Noteworthy Approaches</p> <p>5 Conclusion</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"72 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Recent Advances in Fluoroalkylation Strategies: Exploring Novel Reactivities and Synthetic Applications of Sulfone- and Sulfinate-Based Reagents for Mono-, Di-, and Trifluoromethylations\",\"authors\":\"Alexander Knieb, G. K. Surya Prakash\",\"doi\":\"10.1055/s-0043-1775391\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>Fluoroalkylation serves as a pivotal strategy for chemists to precisely alter the properties of small molecules. Among the established fluoroalkylation protocols, sulfone and sulfinate reagents stand out as versatile tools for these reactions, particularly in mono-, di-, and trifluoromethylations. Their versatility lies in offering multiple pathways, encompassing electrophilic, nucleophilic, as well as radical mechanisms, thus providing diverse routes for controlled molecular modifications through a variety of very exciting mechanistic paths.</p> <p>1 Introduction</p> <p>2 Monofluoromethylation Strategies</p> <p>2.1 Fluorobis(phenylsulfonyl)methane (FBSM)</p> <p>2.2 2-Fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide (FBDT)</p> <p>2.3 Benzothiazole-SO<sub>2</sub>CH<sub>2</sub>F, NaSO<sub>2</sub>CH<sub>2</sub>F, and ClSO<sub>2</sub>CH<sub>2</sub>F</p> <p>2.4 PhSO<sub>2</sub>CH<sub>2</sub>F</p> <p>3 Difluoromethylation Strategies</p> <p>3.1 PhSO<sub>2</sub>CF<sub>2</sub>H</p> <p>3.2 Benzothiazole-SO<sub>2</sub>CF<sub>2</sub>H</p> <p>3.3 2-PyrSO<sub>2</sub>CF<sub>2</sub>H</p> <p>3.4 NaSO<sub>2</sub>CF<sub>2</sub>H</p> <p>4 Trifluoromethylation Strategies</p> <p>4.1 PhSO<sub>2</sub>CF<sub>3</sub>\\n</p> <p>4.2 2-PyrSO<sub>2</sub>CF<sub>3</sub>\\n</p> <p>4.3 Benzothiazole-SO<sub>2</sub>CF<sub>3</sub>\\n</p> <p>4.4 NaSO<sub>2</sub>CF<sub>3</sub>\\n</p> <p>4.4.1 Electrochemical Approaches</p> <p>4.4.2 Photochemical Approaches</p> <p>4.4.3 Other Noteworthy Approaches</p> <p>5 Conclusion</p> \",\"PeriodicalId\":501298,\"journal\":{\"name\":\"Synthesis\",\"volume\":\"72 1\",\"pages\":\"\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-09-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synthesis\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1055/s-0043-1775391\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/s-0043-1775391","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Recent Advances in Fluoroalkylation Strategies: Exploring Novel Reactivities and Synthetic Applications of Sulfone- and Sulfinate-Based Reagents for Mono-, Di-, and Trifluoromethylations
Fluoroalkylation serves as a pivotal strategy for chemists to precisely alter the properties of small molecules. Among the established fluoroalkylation protocols, sulfone and sulfinate reagents stand out as versatile tools for these reactions, particularly in mono-, di-, and trifluoromethylations. Their versatility lies in offering multiple pathways, encompassing electrophilic, nucleophilic, as well as radical mechanisms, thus providing diverse routes for controlled molecular modifications through a variety of very exciting mechanistic paths.
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