Visible light photocatalysis in the late-stage functionalization of pharmaceutically relevant compounds

Chemical Society Reviews, Год журнала: 2020, Номер 50(2), С. 766 - 897

Опубликована: Дек. 22, 2020

Recent developments and future prospects of visible-light photocatalysis in the late-stage functionalization pharmaceuticals natural bioactive compounds.

Язык: Английский

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Three-Component, Interrupted Radical Heck/Allylic Substitution Cascade Involving Unactivated Alkyl Bromides

Journal of the American Chemical Society, Год журнала: 2020, Номер 142(22), С. 10173 - 10183

Опубликована: Май 7, 2020

Developing efficient and selective strategies to approach complex architectures containing (multi)stereogenic centers has been a long-standing synthetic challenge in both academia industry. Catalytic cascade reactions represent powerful means of rapidly leveraging molecular complexity from simple feedstocks. Unfortunately, carrying out Heck-type involving unactivated (tertiary) alkyl halides remains an unmet owing unavoidable β-hydride elimination. Herein, we show that modular, practical, general palladium-catalyzed, radical three-component coupling can indeed overcome the aforementioned limitations through interrupted Heck/allylic substitution sequence mediated by visible light. Selective 1,4-difunctionalization 1,3-dienes, such as butadiene, achieved employing different commercially available nitrogen-, oxygen-, sulfur-, or carbon-based nucleophiles bromides (>130 examples, mostly >95:5 E/Z, >20:1 rr). Sequential C(sp3)–C(sp3) C–X (N, O, S) bonds have constructed efficiently with broad scope high functional group tolerance. The flexibility versatility strategy illustrated gram-scale reaction streamlined syntheses ether, sulfone, tertiary amine products, some which would be difficult access via currently established methods.

Язык: Английский

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Mechanochemistry: New Tools to Navigate the Uncharted Territory of “Impossible” Reactions

ChemSusChem, Год журнала: 2022, Номер 15(17)

Опубликована: Июль 21, 2022

Mechanochemical transformations have made chemists enter unknown territories, forcing a different chemistry perspective. While questioning or revisiting familiar concepts belonging to solution chemistry, mechanochemistry has broken new ground, especially in the panorama of organic synthesis. Not only does it foster "thinking outside box", but also opened reaction paths, allowing overcome weaknesses traditional exactly where use well-established solution-based methodologies rules out progress. In this Review, reader is introduced an intriguing research subject not yet fully explored and waiting for improved understanding. Indeed, study mainly focused on that, although impossible solution, become possible under mechanochemical processing conditions, simultaneously entailing innovation expanding chemical space.

Язык: Английский

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Photocatalytic strategies for the activation of organic chlorides

Nature Catalysis, Год журнала: 2020, Номер 3(11), С. 872 - 886

Опубликована: Ноя. 12, 2020

Язык: Английский

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Photoredox‐Mediated Net‐Neutral Radical/Polar Crossover Reactions

Israel Journal of Chemistry, Год журнала: 2020, Номер 60(3-4), С. 281 - 293

Опубликована: Фев. 18, 2020

Abstract Radical/Polar Crossover (RPC) chemistry is a rapidly growing subset of photoredox catalysis that characterized by transformations featuring both radical and ionic modes reactivity. Net‐neutral RPC particularly interesting in the single‐electron oxidation reduction steps occur through interaction with photocatalyst, thus precluding need for exogenous oxidants or reductants. As such, these facilitate rapid incorporation molecular complexity while maintaining mild reaction conditions. This review covers recent advances photoredox‐mediated net‐neutral synthetic methods, particular emphasis on C–C bond‐forming reactions.

Язык: Английский

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Photocatalytic C(sp³) radical generationviaC–H, C–C, and C–X bond cleavage

Chemical Science, Год журнала: 2022, Номер 13(19), С. 5465 - 5504

Опубликована: Янв. 1, 2022

C(sp 3 ) radicals (R˙) are of broad research interest and synthetic utility.

Язык: Английский

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1,4‐Aminoarylation of Butadienes via Photoinduced Palladium Catalysis

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(14)

Опубликована: Фев. 9, 2024

Abstract A visible‐light‐induced, three‐component palladium‐catalyzed 1,4‐aminoarylation of butadienes with readily available aryl halides and aliphatic amines has been developed, affording allylamines excellent E ‐selectivity. The reaction exhibits exceptional control over chemo‐, regio‐, stereoselectivity, a broad substrate scope, high functional group compatibility, as demonstrated by the late‐stage functionalization bioactive molecules. Mechanistic investigations are consistent photoinduced radical Pd(0)‐Pd(I)‐Pd(II)‐Pd(0) Heck‐Tsuji–Trost allylation cascade.

Язык: Английский

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Visible-Light-Initiated Decarboxylative Alkylation of Quinoxalin-2(1H)-ones with Phenyliodine(III) Dicarboxylates in Recyclable Ruthenium(II) Catalytic System

ACS Sustainable Chemistry & Engineering, Год журнала: 2019, Номер 7(16), С. 14153 - 14160

Опубликована: Июль 15, 2019

A efficient and sustainable approach for the synthesis of 3-alkylquinoxalin-2(1H)-ones has been developed through visible-light-mediated decarboxylative alkylation quinoxalin-2(1H)-ones with phenyliodine(III) dicarboxylates. This photocatalytic reaction could be conducted at ambient temperature by employing eco-friendly PEG-200 as medium. Various were easily obtained present ruthenium(II) catalytic system, which successfully recycled five times without significant decrease its efficiency.

Язык: Английский

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The concept of dual roles design in clean organic preparation

Chinese Chemical Letters, Год журнала: 2019, Номер 30(12), С. 2132 - 2138

Опубликована: Сен. 19, 2019

Язык: Английский

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Photoredox-Catalyzed Sulfonylation ofO-Acyl Oximes via Iminyl Radicals with the Insertion of Sulfur Dioxide

Organic Letters, Год журнала: 2019, Номер 21(13), С. 4950 - 4954

Опубликована: Июнь 10, 2019

A multicomponent sulfonylation of O-acyl oximes via iminyl radicals with the insertion sulfur dioxide under photoredox catalysis is achieved. This reaction oximes, potassium metabisulfite, alkenes, and nucleophiles visible-light irradiation efficient, giving rise to a range sulfones in moderate good yields. broad scope presented functional group compatibility.

Язык: Английский

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