Hydrodifluoromethylation of Alkenes with Difluoroacetic Acid

Meyer, Claudio F.; Hell, Sandrine M.; Misale, Antonio; Trabanco, Andrés A.; Gouverneur, Véronique

doi:10.1002/ange.201903801

Cited by 21 publications

(2 citation statements)

References 49 publications

(10 reference statements)

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“…The decarboxylative alkylation of quinoxalin‐2(1 H )‐ones ( 13 ) with phenyliodine(III)dicarboxylates under visible light was established by He and co‐workers, as an effective and sustainable method for producing 3‐alkylquinoxalin‐2(1 H )‐ones ( 14 and 15 ) in the presence of PIDA (Scheme 2). [82] The optimized reaction parameters are: PIDA (1 equiv. ), Ru(bpy) 3 Cl 2 •6H 2 O (1 mol %) in PEG‐200 and 3 W Blue LED ar RT.…”

Section: Applications Of Phenyliodine(iii)diacetatementioning

confidence: 99%

Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update

et al. 2023

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One of the most widely utilized hypervalent iodines used as an oxidizing agent in organic chemistry is (diacetoxyiodo)benzene (PhI(OAc)2), also known as (DAIB), phenyliodine(III) diacetate (PIDA). In this review, authors have comprehensively and systematically presented the various applications of PIDA in organic synthesis involving C−C, C‐hetero, hetero‐hetero and multiple bond forms from the summer of 2015 to the present. The role of PIDA was also emphasized for the success of particular organic transformation. Recent literature has produced a substantial number of publications (∼100), and this septennial review examines all of the most recent breakthroughs in the field of study.

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Section: Applications Of Phenyliodine(iii)diacetatementioning

confidence: 99%

Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update

et al. 2023

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“…Vicinal carbo-difluoromethylation of widely available alkenes, which results in the simultaneous formation of an alkyl–CF 2 H bond and a C–C bond, is an attractive, efficient, and potentially modular method for the synthesis of complex alkyl-difluoromethanes. Elegant work has recently been conducted by Dolbier 38 , Qing 39 , Xiao 40 , Gouverneur 41 , Zhang 42 , Chu 43 , and others 6 , 44 for the difluoromethylation of alkenes by harnessing the reactivity of an in situ generated difluoromethyl or difluoroalkyl radical. Although these state-of-the-art methods allow for the rapid difluoromethyl-functionalization of alkenes, nonetheless, in these reactions the CF 2 H group is generally attached to the terminal side of the alkenes, as dictated by the CF 2 H radical addition to the less sterically hindered site.…”

Section: Introductionmentioning

confidence: 99%

Copper-catalyzed carbo-difluoromethylation of alkenes via radical relay

et al. 2021

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Organic molecules that contain alkyl-difluoromethyl moieties have received increased attention in medicinal chemistry, but their synthesis in a modular and late-stage fashion remains challenging. We report herein an efficient copper-catalyzed radical relay approach for the carbo-difluoromethylation of alkenes. This approach simultaneously introduces CF2H groups along with complex alkyl or aryl groups into alkenes with regioselectivity opposite to traditional CF2H radical addition. We demonstrate a broad substrate scope and a wide functional group compatibility. This scalable protocol is applied to the late-stage functionalization of complex molecules and the synthesis of CF2H analogues of bioactive molecules. Mechanistic studies and density functional theory calculations suggest a unique ligand effect on the reactivity of the Cu-CF2H species.

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Recent Advances in Mono‐ and Difunctionalization of Unactivated Olefins

et al. 2021

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Olefins are synthetically useful building blocks in modern organic synthesis. Direct functionalization of olefins; represent one of the most explored transformations in synthetic chemistry due to their easy availability and reactivity towards large number of reactants affording diverse range of organic compounds. In recent times, the development of new protocols for the functionalization of olefins is a growing realm. A plethora of olefin functionalization methodologies have been reported in the literature through ionic and free radical mechanisms including single electron transfer (SET) in the last two decades. This review gives an overview of mono-and difunctionalization of unactivated olefins, with an emphasis on the mechanistic details. Functionalization of Unactivated Olefins via Visible-Light Photocatalysis Iridium Photo-Catalyzed Reactions CarbofunctionalizationGlorius and co-workers reported an efficient visible-light mediated three component dicarbofunctionalization of olefins 2 using simple benzylic Katritzky salts 1 as radical precursors (Scheme 1). [8] In this protocol, abundant styrenes, electron-rich heterocycles, and benzylic amines were successfully employed to afford a number of densely functionalized 1,1-diarylalkanes. The optimal reaction conditions for this reaction are [Ir-(dtbbpy)(ppy) 2 ](PF 6 ) (1 mol%) as the photocatalyst in MeCN under irradiation with visible light for 16 h. Under the optimum [a

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Hydrodifluoromethylation of Alkenes with Difluoroacetic Acid

Cited by 21 publications

References 49 publications

Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update

Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update

Copper-catalyzed carbo-difluoromethylation of alkenes via radical relay

Recent Advances in Mono‐ and Difunctionalization of Unactivated Olefins

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