Facile Synthesis of 4‐(Trifluoromethyl)‐1 <i>H</i>‐isochromenes from Alkynols

Ji, Xiao Yue; Siyang, Hai Xiao; Liu, Kai; Jiao, Jia Jun; Liu, Pei Nian

doi:10.1002/ajoc.201500357

Cited by 8 publications

(6 citation statements)

References 80 publications

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“…Synthesis of isochromenes by intramolecular oxytrifluoromethylation described by Liu and coworkers. [55] Scheme 40. Synthesis of regioisomeric isoxazolines by intramolecular oxy-trifluoromethylation described by Tsui and coworkers.…”

Section: Intermolecular Oxy-trifluoromethylationsmentioning

confidence: 99%

“…Similarly, a two‐step one‐pot palladium‐catalyzed oxyzincation/trifluoromethylation of 2‐alkynylbenzyl alcohols was reported to afford 4‐(trifluoromethyl)‐1 H ‐isochromenes (Scheme 39). [55] …”

Section: Oxy‐trifluoromethylationmentioning

confidence: 99%

“… Synthesis of isochromenes by intramolecular oxy‐trifluoromethylation described by Liu and coworkers [55] …”

Section: Oxy‐trifluoromethylationmentioning

confidence: 99%

“…Similarly, a two-step one-pot palladium-catalyzed oxyzincation/trifluoromethylation of 2-alkynylbenzyl alcohols was reported to afford 4-(trifluoromethyl)-1Hisochromenes (Scheme 39). [55] Alternatively, propargyl hydroxylamines could be used as starting materials in the isoxazoline-forming oxy-trifluoromethylation, affording isoxazolines with the CF 3 group directly attached to the heterocyclic core (Scheme 40). [56] In this case, Ruppert-Prakash reagent was used as a trifluoromethylation agent along with stoichiometric amounts of copper and silver compounds and excess amounts of several additives.…”

Section: Intramolecular Oxy-trifluoromethylationsmentioning

confidence: 99%

See 3 more Smart Citations

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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Section: Intermolecular Oxy-trifluoromethylationsmentioning

confidence: 99%

Section: Oxy‐trifluoromethylationmentioning

confidence: 99%

“… Synthesis of isochromenes by intramolecular oxy‐trifluoromethylation described by Liu and coworkers [55] …”

Section: Oxy‐trifluoromethylationmentioning

confidence: 99%

Section: Intramolecular Oxy-trifluoromethylationsmentioning

confidence: 99%

See 2 more Smart Citations

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

et al. 2023

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“…Moreover, Ding and Hou reported a domino trifluoromethylative cyclization of homopropargylamines to form 5-endodihydropyrrolium ions (Scheme , c) . In addition, a method to generate CF 3 -containing isochromenes via alkynol cyclization and subsequent trapping by a CF 3 radical has been described (Scheme , d) . Although these protocols are efficient and versatile, a mild and general method for the synthesis of heteroatom (O, N, and S)-containing rings of various sizes is still highly desirable.…”

mentioning

confidence: 99%

Photoredox-Catalyzed Trifluoromethylative Intramolecular Cyclization: Synthesis of CF₃-Containing Heterocyclic Compounds

Han

Jung

et al. 2018

Org. Lett.

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A general photoredox-catalyzed intramolecular cyclization was developed for the synthesis of trifluoromethylated heterocyclic compounds. The reaction proceeded smoothly under mild photocatalytic conditions with high functional group tolerance, allowing the preparation of oxygen-, sulfur-, or nitrogen-containing heterocycles of different sizes. The broad substrate scope demonstrated the complexity-building potential of the strategy.

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Halogenation and Perfluoroalkylation Chemistry Using Hypervalent Halogen Compounds

Katayev

Jelier

Togni

2018

Patai's Chemistry of Functional Groups

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The introduction of halogenated functional groups by hypervalent iodine(III) reagents has proven to be a popular synthetic method in modern organic chemistry. Such diverse and often unique chemical behavior of iodine(III) compounds originates from their structural and bonding features. In this chapter, we aim to discuss the key structural properties, activation modes, and reactivity trends provided by λ 3 ‐iodane compounds as well as associated challenges therewith. Recent examples of chemo‐, regio‐, and stereoselective iodine(III)‐mediated halogenation and perfluoroalkylation reactions will be presented with an emphasis on contemporary fluorination and trifluoromethylation protocols.

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Facile Synthesis of 4‐(Trifluoromethyl)‐1 H‐isochromenes from Alkynols

Cited by 8 publications

References 80 publications

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

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

Photoredox-Catalyzed Trifluoromethylative Intramolecular Cyclization: Synthesis of CF₃-Containing Heterocyclic Compounds

Halogenation and Perfluoroalkylation Chemistry Using Hypervalent Halogen Compounds

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Facile Synthesis of 4‐(Trifluoromethyl)‐1 H‐isochromenes from Alkynols

Cited by 8 publications

References 80 publications

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

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

Photoredox-Catalyzed Trifluoromethylative Intramolecular Cyclization: Synthesis of CF3-Containing Heterocyclic Compounds

Halogenation and Perfluoroalkylation Chemistry Using Hypervalent Halogen Compounds

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Product

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Photoredox-Catalyzed Trifluoromethylative Intramolecular Cyclization: Synthesis of CF₃-Containing Heterocyclic Compounds