Zinc–Brønsted acid mediated practical hydrotrifluoromethylation of alkenes with CF<sub>3</sub>Br

Peng, Deqian; Wu, Fan; Zhao, Xueqi; Chen, Wei; Yuan, Wen; Zhang, Li; Li, Suhua

doi:10.1039/d1qo01073e

Cited by 19 publications

(13 citation statements)

References 77 publications

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“…Specifically, radical trifluoromethylation has recently received considerable attention along with the rapid development of mild methods to generate trifluoromethyl radical species. 3 Diverse trifluoromethylation reagents including Togni reagents, 4 Umemoto reagents, 5 Ruppert–Prakash reagents (Me 3 SiCF 3 ), 6 Langlois reagent (CF 3 SO 2 Na), 7 CF 3 SO 2 Cl, 8 CF 3 I, 9 and CF 3 Br 10 have been developed as radical trifluoromethyl sources successively. Among these reagents, CF 3 Br is the only one that combines the advantages of low cost and high atom economy.…”

Section: Introductionmentioning

confidence: 99%

Photoinduced Trifluoromethylation with CF₃Br as a Trifluoromethyl Source: Synthesis of α-CF₃-Substituted Ketones

Deng

Wang

et al. 2022

ACS Omega

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An efficient and novel photoinduced trifluoromethylation employing CF 3 Br as a trifluoromethyl source is described. With commercially accessible fac -Ir (III) (ppy) 3 as the catalyst, radical trifluoromethylation between O -silyl enol ether and CF 3 Br occurs successfully. This method provides various α-CF 3 -substituted ketones with a broad substrate scope in good yields under mild reaction conditions.

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Section: Introductionmentioning

confidence: 99%

Photoinduced Trifluoromethylation with CF₃Br as a Trifluoromethyl Source: Synthesis of α-CF₃-Substituted Ketones

Deng

Wang

et al. 2022

ACS Omega

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“…In 2021, Li and coworkers reported a carbanion‐mediated hydro‐trifluoromethylation of alkenes with CF 3 Br in the presence of zinc metal and benzoic acid as a Brønsted acid (Scheme 167). [186] The reaction was proven to proceed via a radical pathway involving the CF 3 radical generated by the benzoic acid‐assisted reduction of CF 3 Br with zinc. Indeed, the reaction did not take place when CF 3 ZnBr ⋅ 2CH 3 CN was used instead of the CF 3 Br/Zn combination.…”

Section: Hydro‐trifluoromethylationmentioning

confidence: 99%

“…Zinc-Brønsted acid-mediated hydro-trifluoromethylation of alkenes. [186] such as temperature, current density, and electrode distance as well as the appropriate choice of substrates. Under the optimized conditions, anodic oxidation generates the CF 3 radical from TFA, while the cathodic reduction and subsequent protonation of the substrate affords an alkyl radical, with the coupling of these two radicals furnishing the desired product.…”

Section: Intermolecular Hydro-trifluoromethylationmentioning

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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“…Hydrofluoroalkylation of alkenes is viewed as an ideal method for the synthesis of fluoroalkylated alkanes as alkenes are among the most abundant carbon feedstocks in organic synthesis. Despite recent progress in hydroperfluoroalkylation, hydrotrifluoromethylation, and hydrodifluoroalkylation of alkenes, the hydromonofluoroalkylation of alkenes is still rarely explored. Recently, Gouverneur developed a hydrofluoromethylation of alkenes with ICH 2 F using (TMS) 3 SiH as a hydrogen atom donor .…”

Section: Introductionmentioning

confidence: 99%

Straightforward Synthesis of Alkyl Fluorides via Visible-Light-Induced Hydromono- and Difluoroalkylations of Alkenes with α-Fluoro Carboxylic Acids

et al. 2022

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We herein report the first visible-light-induced hydromono-and difluoroalkylations of alkenes with inexpensive and easily accessible α-fluoro carboxylic acids. This metal-free protocol exhibits mild conditions, high efficiency, and excellent functional-group tolerance, providing a straightforward approach to mono-and difluoroalkylated alkanes. Moreover, the fluorine effect on the hydrofluoroalkylation reaction is discussed in detail.

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Zinc–Brønsted acid mediated practical hydrotrifluoromethylation of alkenes with CF₃Br

Abstract: We report a mild and efficient hydrotrifluoromethylation of alkenes with bromotrifluoromethane (CF3Br) mediated by zinc and Brønsted acid. This reaction performs well with good functional group compatibility and broad substrate...

Cited by 19 publications

References 77 publications

Photoinduced Trifluoromethylation with CF₃Br as a Trifluoromethyl Source: Synthesis of α-CF₃-Substituted Ketones

Photoinduced Trifluoromethylation with CF₃Br as a Trifluoromethyl Source: Synthesis of α-CF₃-Substituted Ketones

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

Straightforward Synthesis of Alkyl Fluorides via Visible-Light-Induced Hydromono- and Difluoroalkylations of Alkenes with α-Fluoro Carboxylic Acids

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Zinc–Brønsted acid mediated practical hydrotrifluoromethylation of alkenes with CF3Br

Abstract: We report a mild and efficient hydrotrifluoromethylation of alkenes with bromotrifluoromethane (CF3Br) mediated by zinc and Brønsted acid. This reaction performs well with good functional group compatibility and broad substrate...

Cited by 19 publications

References 77 publications

Photoinduced Trifluoromethylation with CF3Br as a Trifluoromethyl Source: Synthesis of α-CF3-Substituted Ketones

Photoinduced Trifluoromethylation with CF3Br as a Trifluoromethyl Source: Synthesis of α-CF3-Substituted Ketones

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

Straightforward Synthesis of Alkyl Fluorides via Visible-Light-Induced Hydromono- and Difluoroalkylations of Alkenes with α-Fluoro Carboxylic Acids

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Product

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Zinc–Brønsted acid mediated practical hydrotrifluoromethylation of alkenes with CF₃Br

Photoinduced Trifluoromethylation with CF₃Br as a Trifluoromethyl Source: Synthesis of α-CF₃-Substituted Ketones

Photoinduced Trifluoromethylation with CF₃Br as a Trifluoromethyl Source: Synthesis of α-CF₃-Substituted Ketones