Photocatalytic C–C Bond Azidation and Cyanation of Acyclic Ketones via a Pro-aromatic Intermediate

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

Published: Jan. 10, 2025

Herein, we report a formal C–C bond azidation and cyanation of unactivated aliphatic ketones using commercially available tosyl azide cyanide, respectively. A visible-light-mediated organophotocatalyst enables radical ketone-derived pro-aromatic dihydroquinazolinones (under mostly redox-neutral conditions) as supported by preliminary mechanistic studies. These metal-free scalable protocols can be used to synthesize tertiary, secondary, primary alkyl azides nitriles with good functional group tolerance postsynthetic diversification the group, including bioconjugation.

Language: Английский

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Benzothiazolines Acting as Carbanion and Radical Transfer Reagents in Carbon–Carbon Bond Construction

Molecules, Journal Year: 2025, Volume and Issue: 30(8), P. 1711 - 1711

Published: April 11, 2025

Traditionally employed as hydrogenation reagents, benzothiazolines have emerged versatile carbanion and radical transfer playing a vital role in the construction of various carbon–carbon bonds. The cutting-edge progress photochemistry chemistry prompted study visible light-driven reactions, bringing into vibrant focus. Their chemical processes been uncovered to encompass variety activation mechanisms, with five distinct modes having identified. This work reviews innovative applications donors alkyl or acyl groups, achieving hydroalkylation hydroacylation substitution. By examining their diverse this review highlights potential serving groups for further research development. Moreover, will offer exemplary inspiration synthetic chemists, contributing ongoing evolution utility organic synthesis.

Language: Английский

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Modular reductive radical-polar crossover-based acyl migration reactions of N-vinylimides with alkyl, silyl, and acyl radicals

RSC Advances, Journal Year: 2025, Volume and Issue: 15(15), P. 11582 - 11586

Published: Jan. 1, 2025

Generation of α-amino ketones: photocatalytic radical addition/acyl migration cascade processes were reported on reactions enamides with dihydroquinazolinones or acyl oxime acetates.

Language: Английский

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Copper‐Catalyzed Aromatization‐Driven Ring‐Opening Amination and Oxygenation of Spiro Dihydroquinazolinones

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(58)

Published: Aug. 8, 2024

Abstract Mild and inexpensive copper‐catalyzed aromatization‐driven ring‐opening amination oxygenation of spiro dihydroquinazolinones are presented, respectively. These protocols provide facile atom‐economical access to the aminated carbonyl‐containing quinazolin‐4(3 H )‐ones in good yields with functional group compatibility, which difficult obtain by conventional methods. Remarkably, a telescoped procedure involving condensation ring‐opening/functionalization for simple cycloalkanone was found be accessible. Mechanistic studies suggest radical pathway this transformation.

Language: Английский

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Deuteration Degree Controllable Synthesis of Aryl Deuteromethyl Ethers Through Dual photoredox and Thiol Catalysis

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(62)

Published: Aug. 22, 2024

Herein, we report a facile and efficient deuteration degree controllable method for the preparation of aryl deuteromethyl ethers through dual photoredox thiol catalysis using phenols as starting materials inexpensive D

Language: Английский

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