Multicomponent Synthesis of Alkyl BCP-Heteroaryls via Electron Donor–Acceptor Complex Photoactivation under Mild Conditions

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1683 - 1696

Published: Jan. 17, 2025

In the vanguard of sustainable chemistry, pursuit efficient pathways for synthesis alkyl bicyclo[1.1.1]pentane-heteroaryls has captured attention scientific vanguard. We herein report a groundbreaking and eco-conscious multicomponent coupling reaction that paves way alkylation heteroarylation [1.1.1]propellane, process uniquely enabled by photochemical prowess an electron donor–acceptor (EDA) complex. This method is distinguished its minimalist yet powerful approach: devoid transition metals, additives, photosensitizers. Its universality further exemplified seamless compatibility broad spectrum halides heteroarenes under standardized conditions, heralding new era synthetic versatility. The method's practicality underscored capacity late-stage modification pharmaceuticals, offering transformative tool enhancement existing drug molecules. Moreover, facile derivatization synthesized products underscores adaptability potential diverse applications. Our mechanistic studies have elucidated underlying radical-relay pathway, pinpointing pivotal role EDA complex in initiating transformation. discovery not only enriches our fundamental understanding but also opens avenues strategic optimization.

Language: Английский

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Merging Photoinduced Electron Transfer with Hydrogen Atom Transfer: Formal β-C(sp³)–H Pyridination of Carbonyls

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

Published: Jan. 9, 2025

In this study, a novel approach that combines photoinduced electron transfer (ET) with hydrogen atom (HAT) has been introduced for the selective β-C(sp3)–H pyridination of carbonyl compounds. This method is notable its absence transition metals and ability to function under benign reaction conditions, resulting in range pyridinated derivatives consistently moderate good yields. The significance technique further underscored by potential late-stage functionalization pharmaceutically significant molecules. Mechanistic investigations confirmed proceeds via radical-mediated pathway.

Language: Английский

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Visible-Light-Induced Divergent C–H Esterification/Alkylation of Quinoxalin-2(1H)-ones with Aldehydes under Mild Conditions

Organic Letters, Journal Year: 2025, Volume and Issue: 27(10), P. 2526 - 2531

Published: March 5, 2025

Herein, we introduce an efficient and straightforward strategy for the selective C-H esterification alkylation of quinoxalin-2(1H)-ones with aldehydes. A key feature our study is ability to perform both using different types The reaction system highly compatible a range aldehydes, yielding C3-esterified C3-alkylated products in moderate-to-good yields. applicability this approach further enhanced by its scalability through continuous-flow synthesis, late-stage modification significant molecules, product derivatization. Our mechanistic investigations reveal radical relay mechanism, triggered hydrogen atom transfer process.

Language: Английский

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Energy-transfer photocatalysis for Minisci C–H (amino)alkylation of heteroarenes using oxime esters as dual-role reagents

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5122 - 5129

Published: Jan. 1, 2024

This study demonstrates a strategy involving photoinduced energy transfer for decarboxylative Minisci C–H (amino)alkylation of heteroarenes employing diverse oxime esters (from carboxylic acids) as (amino)alkylating reagents.

Language: Английский

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Transition-metal-, oxidant- and additive-free multi-component synthesis of alkyl heteroaryl BCPs enabled by visible-light-induced phosphine-catalyzed halogen-atom transfer

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

This study describes a pioneering visible-light-induced phosphine-catalyzed halogen-atom transfer (XAT) strategy that heralds new era in the difunctionalization of [1.1.1]propellane.

Language: Английский

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Synthesis of Nafimidone Derivatives by Visible-Light-Induced α-C—H Functionalization of Carbonyl

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 677 - 677

Published: Jan. 1, 2025

Language: Английский

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Heterogeneous g-C₃N₄/NaI Dual Catalytic Difunctionalization of Alkenes with Heteroarenes and Methyl Carbazate under Visible Light

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

Published: April 26, 2025

Herein, a photoinduced heterogeneous catalytic system merging g-C3N4 and NaI has been established for the difunctionalization of alkenes in conjunction with heteroarenes methyl carbazate. This approach is notable its broad substrate tolerance, encompassing wide range leading to formation corresponding esters moderate good yields. Additionally, scalability synthetic process versatility product transformations have illustrated, highlighting potential practical application organic synthesis.

Language: Английский

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Recyclable V₂O₅/g-C₃N₄ Heterojunction-Catalyzed Visible-Light-Promoted C3–H Trifluoromethylation of Quinoxalin-2-(1H)-ones

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(13), P. 9543 - 9550

Published: June 14, 2024

A visible-light-initiated C-H trifluoromethylation of quinoxalin-2(1

Language: Английский

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Self-Catalyzed Sono-Photoinduced Arylation of Quinoxalin-2(1H)-ones with Arylhydrazines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 25, 2024

Herein, the first example of self-catalyzed sono-photoinduced carbon-carbon bond formation was described. Combining advantages phototriggered self-catalysis and ultrasonic catalysis, a wide range 3-arylquinoxalin-2(1

Language: Английский

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Decatungstate-photocatalyzed tandem acylation/cyclization/self-hydrogenation of isocyanides with aldehydes to hydroxyalkylated N-heteroarenes via multiple hydrogen atom transfer

Green Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A 100% atom economical construction of hydroxyalkylated N-heteroarenes through decatungstate-catalyzed tandem cyclization/self-hydrogenation isocyanides and aldehydes under exogenous hydrogen reagent- byproduct-free conditions was developed.

Language: Английский

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