Photocatalytic Oxidative C(sp³)-H/N–H Cross-Dehydrogenative Coupling of Tertiary Anilines with Amides/Imides: Synthesis of N-Mannich Bases

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

Published: April 30, 2025

A photocatalytic method for the synthesis of N-Mannich bases has been developed through C(sp3)-H/N-H cross-dehydrogenative coupling N,N-dimethylanilines with amides/imides. This process utilizes 2,4,6-triphenylpyrylium tetrafluoroborate (TPT) as photocatalyst and is conducted at ambient temperature atmospheric air. Various aromatic, heteroaromatic aliphatic (cyclic) amides, well imides were successfully employed, yielding moderate to good results. Preliminary mechanistic isotope-labeling studies indicate that reaction likely proceeds via a single electron transfer pathway involves an α-aminoalkyl radical intermediate.

Language: Английский

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Iodine-Catalyzed Room-Temperature Aerobic Oxidation of C(sp³)–H Bonds and Its Application in the Synthesis of Quinoxaline Derivatives

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

Published: May 1, 2025

An iodine-catalyzed aerobic oxidation reaction of C(sp3)-H bonds was established at room temperature. In this transformation, iodine acts as a Lewis acid catalyst, and the pyridine moiety in substrate plays crucial role. Under optimum conditions, picolyl ketone substrates were smoothly transformed into corresponding 1,2-dicarbonyl compounds, subsequent introduction 1,2-diaminobenzenes mixture led to formation various quinoxaline derivatives. This synthetic process does not use transition metals also features mild operational simplicity, gram-scale synthesis.

Language: Английский

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Iodine-Mediated δ-Amination of sp³ C–H Bonds

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3481 - 3490

Published: Feb. 21, 2024

We present a direct δ-amination reaction of sp

Language: Английский

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Copper‐Catalyzed α‐Indolmethylation of 2‐Pyridylacetates with 3‐Indoleacetic Acids via Alkylideneindolenine Intermediates

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(11), P. 2602 - 2606

Published: April 13, 2024

Abstract This study reports the copper‐catalyzed α‐indolmethylation of 2‐pyridylacetates with 3‐indoleacetic acids. reaction offers an approach to generating alkylideneindolenine electrophiles via oxidative decarboxylation The developed system demonstrates good versatility, extending beyond indolmethylation include activated esters and nitroalkanes. Moreover, a biological evaluation revealed that several products exhibited antiproliferative activity against different cancer cell lines.

Language: Английский

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Cascade [3 + 2] Annulation of 1,3-Dicarbonyl Compounds and Ethyl Secondary Amines for Pyrrole Synthesis via Poly C(sp³)–H Bond Functionalization

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 16049 - 16054

Published: Oct. 21, 2024

The synthesis of polyfunctionalized pyrroles via the cascade reactions 1,3-dicarbonyl compounds and two molecules ethyl secondary amines has been realized simple iodine catalysis in presence Dess-Martin periodinane (DMP). formation target pyrrole products involves one new C-C C-N bonds major functionalization six C(sp

Language: Английский

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I2-Catalyzed Cascade Annulation of 2-(Pyridin-2-Yl)Acetate Derivatives with N,N-Dimethylenamine Ketones: Site-Selective Synthesis of Functionalized Indolizines

Published: Jan. 1, 2024

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Language: Английский

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I2-Catalyzed cascade annulation of 2-(pyridin-2-yl)acetate derivatives with ,-dimethylenamine ketones: site-selective synthesis of functionalized indolizines

Tetrahedron, Journal Year: 2024, Volume and Issue: 159, P. 134015 - 134015

Published: May 3, 2024

Language: Английский

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