Recent Advances on the Halo- and Cyano-Trifluoromethylation of Alkenes and Alkynes

Fu, Bo; Escorihuela, Jorge; Han, Jianlin; Fustero, Santos; Barrio, Pablo; Sodeoka, Mikiko; Kawamura, Shintaro; Sorochinsky, Alexander E.; Soloshonok, Vadim A.

doi:10.3390/molecules26237221

Cited by 20 publications

(9 citation statements)

References 118 publications

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“…The simultaneous addition of trifluoromethyl and cyano groups onto carbon-carbon double and triple bonds is a widely developed strategy of modern organic syntheses. In 2021, Han [63] et al reported the recent advances on the halo-and cyanotrifluoromethylation of alkenes and alkynes summarizing the most significant contributions made in this area until 2021. Therefore, this chapter discusses only applications not included in this report.…”

Section: Cyanotrifluoromethylation Reactionsmentioning

confidence: 99%

Carbotrifluoromethylations of C−C Multiple Bonds (Excluding Aryl‐ and Alkynyltrifluoromethylations)

Aradi

Kiss

2023

Chemistry A European J

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Organofluorine chemistry has become an expanding area of research in organic chemistry and drug design. The synthesis of fluorine-containing molecules has received high significance in synthetic chemistry. Trifluoromethylative difunctionalizations of carbon-carbon multiple bonds with the simultaneous introduction of a CF 3 group and another function have considerable relevance. Because of the high importance of carbon-carbon bond-forming reactions in organic synthesis, carbotrifluoromethylations are considered to be a field of synthetic chemistry of increasing importance. Our current goal in this review is to summarize recent developments of various trifluoromethylation reactions (excluding aryl-and alkynyl-trifluoromethylations) taking into consideration several main approaches, such as alkenyltrifluoromethylation, alkyltrifluoromethylation, carbonyltrifluoromethylation, and cyanotrifluoromethylation reactions.

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Section: Cyanotrifluoromethylation Reactionsmentioning

confidence: 99%

Carbotrifluoromethylations of C−C Multiple Bonds (Excluding Aryl‐ and Alkynyltrifluoromethylations)

Aradi

Kiss

2023

Chemistry A European J

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“…[11][12][13] Considering the importance of carbon-carbon bond-forming reactions in organic synthesis, carbotrifluoromethylations (Scheme 3) are worth more attention (currently, only aryltrifluoromethylation has an extensive literature). Because of the pseudohalogen nature of the nitrile group, cyanotrifluoromethylations [30] were omitted on Scheme 3.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Developments in the Alkynyltrifluoromethylations of Alkenes and Alkynes

et al. 2022

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As a consequence of the expanding relevance of fluorine-containing organic molecules in drug research, the synthesis of organofluorine scaffolds has received high significance in synthetic organic chemistry. Trifluoromethylative difunctionalizations of carbon–carbon multiple bonds, with the simultaneous introduction of a CF3 group and another function, have considerable potential. Considering the high importance of carbon–carbon bond-forming reactions in organic synthesis, carbotrifluoromethylations and, in particular, alkynyltrifluoromethylations are considered to be increasing areas of synthetic chemistry. Alkynyltrifluoromethylation is a narrow segment and a relatively new approach in synthetic chemistry, however it has not been reviewed so far. Therefore, our goal in the current minireview is to summarize the recent developments of alkynyltrifluoromethylation reactions taking into consideration several main aspects, such as (a) alkynyltrifluoromethylation reactions of alkenes including (i) reactions involving intramolecular alkynyl migration and (ii) intermolecular transformations as well as (b) alkynyltrifluoromethylation reactions of alkynes.

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“…[12] Furthermore, although many related reviews have been published after 2015, almost all of them are short reviews, [13] personal accounts, [14] or cover only specific topic such as photochemical reactions [15] and halo-trifluoromethylations. [16] Among the various difunctionalizative trifluoromethylation reactions, this review focuses on those accompanied by the formation of polar CÀ heteroatom (O, N, S, Se, B) or CÀ H bonds, as they provide useful CF 3 -substituted building blocks. Moreover, we aim to systematically map the reported variants of such trifluoromethylations, taking a bird's eye view of reaction conditions, modes, and mechanisms to identify the related evolution trends and future prospects.…”

Section: Introductionmentioning

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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Recent Advances on the Halo- and Cyano-Trifluoromethylation of Alkenes and Alkynes

Cited by 20 publications

References 118 publications

Carbotrifluoromethylations of C−C Multiple Bonds (Excluding Aryl‐ and Alkynyltrifluoromethylations)

Carbotrifluoromethylations of C−C Multiple Bonds (Excluding Aryl‐ and Alkynyltrifluoromethylations)

Developments in the Alkynyltrifluoromethylations of Alkenes and Alkynes

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

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