Intermolecular oxidative radical fluoroalkylfluorosulfonylation of unactivated alkenes with (fluoroalkyl)trimethylsilane, silver fluoride, sulfur dioxide and <i>N</i>-fluorobenzenesulfonimide

Lin, Qiongzhen; Liu, Yongan; Xiao, Zhiwei; Zheng, Liping; Zhou, Xiumiao; Guo, Yong; Chen, Qing‐Yun; Zheng, Changge; Liu, Chao

doi:10.1039/c8qo01192c

Cited by 51 publications

(13 citation statements)

References 61 publications

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“…The reaction is supposed to proceed through thermal dediazotization of arenediazonium salts and subsequent nucleophilic fluorination with a fluorine ion to form a C Ar –F bond. More recently, we developed an efficient method for the preparation of a number of alkyl sulfonyl fluorides via novel radical SO 2 insertion and in situ fluorination . On the basis of these findings and as an extension of our interest in fluorosulfonylation, it is reasonable to conceive that the C Ar –S(VI)–F bond construction might be achieved with arenediazonium salts in combination with sulfur dioxide and fluoride salt under appropriate reaction conditions (Figure c), which is a new mode of construction of arenesulfonyl fluorides.…”

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confidence: 99%

Arenesulfonyl Fluoride Synthesis via Copper-Catalyzed Fluorosulfonylation of Arenediazonium Salts

et al. 2020

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We report herein a general and practical copper-catalyzed fluorosulfonylation reaction of a wide range of abundant arenediazonium salts to smoothly prepare various arenesulfonyl fluorides using the 1,4-diazabicyclo[2.2.2]octane-bis(sulfur dioxide) adduct as a convenient sulfonyl source in combination with KHF2 as an ideal fluorine source and without the need for additional oxidants. Interestingly, the electronic character of the arene ring in the starting arenediazonium salts has a significant impact on the reaction mechanistic pathway.

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Arenesulfonyl Fluoride Synthesis via Copper-Catalyzed Fluorosulfonylation of Arenediazonium Salts

et al. 2020

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“…In 2019, Zheng, Liu and coworkers reported the thio‐trifluoromethylation of alkenes with Ruppert‐Prakash reagent (Scheme 134a) [153] based on the principle of their previous thio‐trifluoromethylation using Ag(O 2 CCF 2 SO 2 F) (Scheme 126). In this reaction, AgCF 3 generated in situ as the active species from Ruppert‐Prakash reagent and AgF reacts with alkenes in the presence of DABSO and NFSI to afford a wide variety of CF 3 ‐containing sulfonyl fluorides.…”

Section: Thio‐/seleno‐trifluoromethylationmentioning

confidence: 99%

“…Thio-trifluoromethylation of alkenes with Ruppert-Prakash reagent/AgF. [153,154] vinyl radical that reacts with bpyCu II (CF 3 )(OSO 3 H) to generate the desired product via coupling.…”

Section: Reactions Using External Sulfur Sources In Addition To Trifl...mentioning

confidence: 99%

Evolution and Future of Hetero‐ and Hydro‐Trifluoromethylations of Unsaturated C−C Bonds

et al. 2023

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The difunctionalizative trifluoromethylation of unsaturated CÀ C bonds is a highly useful and efficient method for the synthesis of trifluoromethyl compounds with attractive architectures from simple feedstocks, allowing the introduction of the CF 3 group along with a wide variety of substituents either inter-or intramolecularly. Given that trifluoromethyl molecules are increasingly used as promising bioactive species in the design of new drugs and agrochemicals, difunctionalizative trifluoromethylation has been extensively studied during the last decade. This review focuses on reactions proceeding via the simultaneous formation of CÀ heteroatom (O, N, S, Se, B) and CÀ H bonds, as these reactions provide useful CF 3 group-containing building blocks. To identify the trends and prospects of the evolution of this methodology, we systematically describe the variants of these types of reactions and provide a more general view of reaction conditions, modes, and mechanisms. The presented comprehensive survey enables the categorization of reactions into those that are synthetically mature and those with room for further development. 1.Shintaro Kawamura completed his Ph.D. at Kyoto University in 2013 under the supervision of Prof. Masaharu Nakamura. Since 2012, he has worked in Prof. Mikiko Sodeoka's group at RIKEN. He was promoted from a postdoctoral researcher to a Research Scientist (2017) and then to a Senior Research Scientist (2021) at RIK-EN. Dr. Kawamura's research interests include fluoroalkylation reactions based on the precise reactivity control of radical species. Pablo Barrio completed his Ph.D. at the University of Oviedo in 2007 under the supervision of Prof. Barluenga. After a postdoctoral role in the group of Prof. Carreira at ETH Zurich, he joined the group of Prof. Fustero in 2009 as a Juan de la Cierva Fellow, working for several years in the field of organofluorine chemistry. In 2018, he moved to Oviedo as a Ramón y Cajal Fellow, joining the Selective Organic Synthesis (SOS) group. Dr. Barrio's research interests include gold catalysis. Santos Fustero studied Chemistry at the University of Zaragoza, where he obtained his B.S. and Ph.D. under the supervision of Prof. Barluenga and Prof. Gotor. He spent two years as a postdoctoral research associate at Prof. Lehmkuhl's laboratory at Max-Planck-Institut für Kohlenforschung in Mülheim an der Ruhr, Germany. In 1983, he became Associate Professor at the University of Oviedo, Spain, and was promoted to Full Professor at the University of Valencia in 1990. In 2005, he became a research group leader at Centro de Investigación Príncipe Felipe in Valencia. Prof. Fustero's research interests include organofluorine and medicinal chemistry, organocatalysis, heterocyclic chemistry, and new reaction methodologies. Jorge Escorihuela received his Ph.D. in Chemistry at Universitat Jaume I (Castellon, Spain) in 2009. After a postdoctoral stage at Universitat Politècnica de València (UPV), he worked at Wageningen University and Research (the Netherlands) with Prof. Zuilho...

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“…59–61 Synthetic methods via radical sulfur dioxide insertion/fluorination also provide aliphatic sulfonyl fluorides. 62–65…”

Section: Aliphatic Fluorosulfonylationmentioning

confidence: 99%

Synthetic strategies for fluorosulfonylated compounds: application to click chemistry reactions

Barata‐Vallejo

Yerien

Postigo

2023

Catal. Sci. Technol.

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Intermolecular oxidative radical fluoroalkylfluorosulfonylation of unactivated alkenes with (fluoroalkyl)trimethylsilane, silver fluoride, sulfur dioxide and N-fluorobenzenesulfonimide

Abstract: Reaction of unactivated alkenes affords various fluoroalkyl-containing alkyl sulfonyl fluorides with good functional group tolerance under mild conditions.

Cited by 51 publications

References 61 publications

Arenesulfonyl Fluoride Synthesis via Copper-Catalyzed Fluorosulfonylation of Arenediazonium Salts

Arenesulfonyl Fluoride Synthesis via Copper-Catalyzed Fluorosulfonylation of Arenediazonium Salts

Evolution and Future of Hetero‐ and Hydro‐Trifluoromethylations of Unsaturated C−C Bonds

Synthetic strategies for fluorosulfonylated compounds: application to click chemistry reactions

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