Photoredox Defluorinative Alkylation of 1‐Trifluoromethyl Alkenes and 1,3‐Butadienes with 1,4‐Dihydropyridines as Alkylation Reagents

Chen, Haoguo; Anand, Devireddy; Zhou, Lei

doi:10.1002/ajoc.201900026

Cited by 46 publications

(19 citation statements)

References 55 publications

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“…In 2019, Zhou disclosed a simple and mild conversion of the photocatalytic defluorinative alkylation of 1‐trifluoromethyl alkenes 102 using 1,4‐DHP 103 as the alkyl donors (Scheme 20). [35] A series of alkylated 1,1‐difluoroalkenes 104 were achieved in moderate to high yields through a sequential C−C bond and C−F bond cleavage process. Beyond 1‐trifluoromethyl alkenes as the reaction partners, 1‐trifluoromethyl‐1,3‐butadienes were also employed for the first time using this method to deliver conjugated 1,1‐difluorodienes in good yields.…”

Section: Defluorinative Functionalization Of Trifluoromethylalkenesmentioning

confidence: 99%

Recent Advances in the Synthesis of Difluorinated Architectures from Trifluoromethyl Groups

2021

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Fluorine-containing moieties are widely used in the pharmaceutical, agrochemical, and material fields. Thus, these structures are of immense interest in the fields of organic synthesis and medicinal chemistry. Among various fluorinated groups, the difluoromethyl unit has drawn increasing attention due to its unique pharmaceutical properties. In recent years, several methods for the synthesis of difluoromethylated compounds have been rapidly developed. However, most of these methods treat aromatic compounds with excess difluoromethylating reagents, which often contain organometallic compounds, so these transformations are generally less environmentally friendly and atom-economical. In this review, we summarize the recent development of new methods for the synthesis of difluoromethyl motifs or difluoroalkenes from trifluoromethylated aromatic compounds or trifluoromethyl alkenes via single C(sp 3 )À F bond cleavage.1.

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Section: Defluorinative Functionalization Of Trifluoromethylalkenesmentioning

confidence: 99%

Recent Advances in the Synthesis of Difluorinated Architectures from Trifluoromethyl Groups

2021

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“…Similar protocols have been developed for the photo-induced generation of alkyl radicals from alkyl-DHPs for addition to different substrates such as imines, 102 1-trifluoromethyl alkenes, 103 brominated alkynes 104 or diazonium salts. 105…”

Section: Pyridine Derivativesmentioning

confidence: 99%

Boron, silicon, nitrogen and sulfur-based contemporary precursors for the generation of alkyl radicals by single electron transfer and their synthetic utilization

2022

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“…These reagents are also available for the C-F bond transformation of -trifluoromethyl alkenes 77. 38,39 Primary and secondary alkyl groups can be installed into gem-difluoroalkene frameworks via radical addition and sequential -fluoride elimination.…”

Section: Scheme 19 Organometallic Reagents For the Generation Of Carb...mentioning

confidence: 99%

C(sp3)–F Bond Transformation of Perfluoroalkyl Compounds Mediated by Visible-Light Photocatalysis: Spin-Center Shifts and Radical/Polar Crossover Processes via Anionic Intermediates

2022

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Precisely controllable C–F bond activation is a significant challenge in organic synthesis due to its large bond energy. A single C(sp3)–F bond transformation of perfluoroalkyl groups is particularly desirable to supply functionalized perfluoroalkyl compounds offering properties that could be significantly useful in pharmaceutical and materials chemistry. Recently, the single defluoronative transformation of perfluoroalkyl compounds was developed via visible-light photocatalysis. Herein, we summarize this field via two main topics. Topic 1 involves the transformation of C(sp3)–F bonds in either perfluoroalkylarenes or perfluoroalkane carbonyl compounds via a defluorinative spin-center shift in the radical anion intermediates. Topic 2 addresses the defluorinative transformation of α-trifluoromethyl alkenes to gem-difluoroalkenes via a radical/polar crossover process.

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Photoredox Defluorinative Alkylation of 1‐Trifluoromethyl Alkenes and 1,3‐Butadienes with 1,4‐Dihydropyridines as Alkylation Reagents

Cited by 46 publications

References 55 publications

Recent Advances in the Synthesis of Difluorinated Architectures from Trifluoromethyl Groups

Recent Advances in the Synthesis of Difluorinated Architectures from Trifluoromethyl Groups

Boron, silicon, nitrogen and sulfur-based contemporary precursors for the generation of alkyl radicals by single electron transfer and their synthetic utilization

C(sp3)–F Bond Transformation of Perfluoroalkyl Compounds Mediated by Visible-Light Photocatalysis: Spin-Center Shifts and Radical/Polar Crossover Processes via Anionic Intermediates

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