Photoredox-Catalyzed Alkene Acylesterification with Acyloxime Esters via C–C and Tertiary C–O Bond Formation

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 7, 2025

We describe an efficient acyl esterification method for alkenes utilizing acyloxime esters as bifunctional reagents featuring radical acylation and congested C–O bond formation. This approach is characterized by mild photoredox conditions, high step atom economy, a broad substrate scope, excellent regioselectivity. A variety of valuable α-acyl hindered alcohol esters, including those obtained via gram-scale synthesis late-stage functionalization pharmaceutical molecules, were presented, demonstrating its synthetic potential practicability.

Language: Английский

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Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(11), P. 110024 - 110024

Published: May 17, 2024

Language: Английский

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I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 36(1), P. 109799 - 109799

Published: March 20, 2024

Language: Английский

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Photocatalytic Sulfonylation: Innovations and Applications

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: July 14, 2024

Photosynthesis, converting sustainable solar energy into chemical energy, has emerged as a promising craft to achieve diverse organic transformations due its mild reaction conditions, sustainability, and high efficiency. The synthesis of sulfonated compounds drawn significant attention in the pharmaceuticals, agrochemicals, materials industries unique structure electronic properties sulfonyl groups. Over past decades, many photocatalytic sulfonylation reactions have been developed. In this review, recent advances photocatalyzed reviewed since 2020, with primary focus on discussing design mechanism.

Language: Английский

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Construction of β-Oximino Phosphorodithioates via (2,2,6,6-Tetramethylpiperidin-1-yl)oxyl-Promoted Difunctionalization of Alkenes with tert-Butyl Nitrite, P₄S₁₀, and Alcohols

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3883 - 3888

Published: April 29, 2024

A (2,2,6,6-tetramethylpiperidin-1-yl)oxyl-mediated difunctionalization of alkenes with

Language: Английский

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An Iron‐Catalyzed Three‐Component Radical Cascade Cyclization to Access Cyanoalkylsulfonyl Quinolino‐Quinazolinones

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(11), P. 2456 - 2460

Published: March 21, 2024

Abstract An iron(II)‐catalyzed cascade reaction, involving cyanoalkylsulfonylation and cyclization, has been devised to enable the synthesis of functionalized sulfonylated quinolino‐quinazolinone alkyl nitriles. This three‐component radical transformation exhibits excellent chemo‐ regioselectivity while functioning without need for external oxidizing or reducing agents. The cost‐effectiveness this catalytic system, together with its broad substrate application, which includes drug molecule derivatives, make approach efficient adaptable.

Language: Английский

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Alkylazolation of Alkenes via Photocatalytic Radical Polar Crossover

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 13, 2025

We present a photocatalytic method for alkylamination of alkenes, enabling efficient C-C and C-N bond formation to construct aza-heterocycles valuable in drug discovery. Using radical-polar crossover pathway, electron-deficient alkenes are reduced electrophilic radicals, which react with electron-rich form nucleophilic radicals. Oxidation these intermediates yields carbocations, trapped by aza-heteroarenes afford alkylaminated products. This strategy enhances molecular complexity while suppressing side reactions.

Language: Английский

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Visible-Light-Induced 4CzIPN-Catalyzed Alkylamination of Alkenes via Cyclobutanone Oxime Esters and Anilines

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

We disclosed an organophotoredox-catalyzed three-component oxidative radical-polar crossover strategy for constructing 1,2-alkylamination products. Cycloketone oxime derivatives were used as cyanoalkyl radical precursors and anilines the nucleophiles. This facile protocol shows a good reaction yield broad substrate scope.

Language: Английский

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Visible-light-induced photocatalyst-free cascade cyclization of 3-(2-(ethynyl)phenyl)quinazolinones to sulfonated quinolino[2,1-b]quinazolinones

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(56), P. 7228 - 7231

Published: Jan. 1, 2024

A visible-light-induced K 2 S O 8 -promoted cascade sulfonation/cyclization reaction to afford a series of sulfonated quinolino[2,1- b ]quinazolinones has been developed under mild conditions.

Language: Английский

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Visible‐Light Promoted Minisci–Type Cyanoalkylation of Azauracils via C−C Bond Cleavage

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(22)

Published: March 16, 2024

Abstract A photo‐induced Minisci–type cyanoalkylation of azauracils was developed under metal‐free and base‐free conditions. Readily available cyclobutanone oxime esters were used as the cyanoalkylating reagents via C−C bond cleavage to generate γ‐cyanoalkyl azauracil derivatives in good moderate yields. The introduced cyano group can be easily converted into many other functional groups, thus makes current protocol more practical.

Language: Английский

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