Photoinitiated stereoselective direct C(sp²)–H perfluoroalkylation and difluoroacetylation of enamides

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(15), С. 4086 - 4094

Опубликована: Янв. 1, 2021

Photoinitiated regio- and stereoselective C(sp²)–H perfluoroalkylation difluoroacetylation of enamides are developed, furnishing biologically physiologically privileged fluoro-containing enamide scaffolds.

Язык: Английский

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Visible light-mediated metal-free alkyl Suzuki–Miyaura coupling of alkyl halides and alkenylboronic acids/esters: a green method for the synthesis of allyl difluoride derivatives

Green Chemistry, Год журнала: 2023, Номер 25(9), С. 3453 - 3461

Опубликована: Янв. 1, 2023

Halogen bonding-assisted C sp 3 –Br homolysis and bromine radical-mediated oxidative deboronation make visible-light-driven photocatalyst-free alkyl Suzuki–Miyaura coupling of alkenylboronic acids/esters with α-bromodifluoroacylarenes accessible.

Язык: Английский

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Fluoroalkyl Iodides in Fluoroalkylative Difunctionalization of C−C Multiple Bonds

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(13), С. 2092 - 2125

Опубликована: Май 16, 2023

Abstract Fluorinated alkyl iodides serve as a convenient and inexpensive source of fluoroalkyl radicals that can readily undergo addition to the C−C unsaturated bonds alkynes alkenes which is foundation for variety useful synthetic protocols. Since 2010 this field has witnessed huge progress in several respects. First portfolio fluorinated was extended beyond only simple perfluoroalkyl (C n F 2n+1 I). In particular, employment iododifluoro−methyl‐ carbonyls phosphonates enabled facile installation medicinally relevant difluoromethylene motif. Secondly, from conceptual point view, novel strategies activation towards radical formation have been introduced, relying on electron donor‐acceptor (EDA) complexes, photoredox catalysis, frustrated Lewis pairs transition metal complementing prior approaches based heat UV induced C−I homolysis, initiators, transfer processes. Based these range fluoroalkylative transformations systems added classical iodoperfluoroalkylation. Broadly applicable protocols fluoroalkylation hydrofluoroalkylation, well more sophisticated, complexity‐building methods fluoroalkylation‐annulation tandem multicomponent fluoroalkylations with concomitant another functionality recently disclosed. This review summarizes achieved since reactivity emphasis placed above‐mentioned advances.

Язык: Английский

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Regio- and stereoselective access to highly substituted vinylphosphine oxides via metal-free electrophilic phosphonoiodination of alkynes

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Июнь 25, 2024

Abstract In general, the P-centered ring-opening of quaternary phosphirenium salts (QPrS) predominantly leads to hydrophosphorylated products, while C-centered is primarily confined intramolecular nucleophilic reactions, resulting in formation phosphorus-containing cyclization products instead difunctionalized generated through intermolecular processes. Here, promotion three-member rings by iodine anions and quenching electronegative carbon atoms cations, we successfully synthesize β -functionalized vinylphosphine oxides P-addition QPrS intermediates situ. Multiple β- iodo-substituted can be obtained with exceptional regio- stereo-selectivity reacting secondary phosphine unactivated alkynes. addition, a variety converted from C-I bonds, especially rapid construction benzo[ b ]phospholes oxides, demonstrates significance this strategy.

Язык: Английский

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Construction of sterically congested oxindole derivatives via visible-light-induced radical-coupling

Chemical Science, Год журнала: 2021, Номер 12(46), С. 15399 - 15406

Опубликована: Янв. 1, 2021

Simple, modular assembly of complex fluoroalkyl-containing oxindole derivatives with a broad scope and excellent functional group tolerance under mild conditions (metal- photocatalyst-free). Benzyl iodides were identified as key intermediates.

Язык: Английский

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