Silver‐Catalyzed Decarboxylative Coupling of Oxamic Acids with Styrenes to Synthesize E‐Cinnamamides: A Distinguish Reaction Pathway

ChemistryOpen, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 29, 2025

Abstract A silver‐catalyzed decarboxylative coupling of oxamic acids with styrenes has been developed to produce E ‐cinnamamides. Oxamic act as efficient precursors for carbamoy radicals. Based on the mechanistic experiments and intermediate analysis, proposed mechanism involves radical addition styrenes, followed by oxidation solvent participation, ultimately leading formation cinnamamides which is different from reported cases.

Language: Английский

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Photocatalytic Pyridyl-carbamoylation of Alkenes for Accessing β-Pyridyl Amides

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

Published: March 7, 2025

The β-pyridyl amide is a critical scaffold in medical discovery yet lacks efficient synthetic methods. Here, we describe, for the first time, visible-light-induced, redox-neutral radical cross-coupling reaction involving alkenes, oxamic acids, and cyanopyridines that offers versatile assembly of β-pyridylamides. This approach features mild conditions, high step efficiency, substrate breadth, providing green strategy alkene pyridyl-carbamoylation. Achieving this transformation relies on catalytic system, which adeptly avoids competing nucleophilic carbamoyl with electrophilic pyridyl radical, enabling three-component tandem process chemoselectivity.

Language: Английский

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Photoinduced Carbamoylarylation of Alkynes with N-Aryl Oxamic Acids

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

Published: April 2, 2025

1,2-Difunctionalization of alkynes is an attractive synthetic protocol, because it can achieve a high step economy and provide various complex organic molecules. This study demonstrates the visible-light-induced carbamoylarylation terminal using N-aryl oxamic acids as bifunctional reagents. The transformation involves addition carbamoyl radicals to alkenes, resulting in 1,4-aryl migration via C(aryl)-N bond cleavage afford corresponding arylacrylamides moderate good yields.

Language: Английский

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CO2-promoted photocatalytic aryl migration from nitrogen to carbon for switchable transformation of N-arylpropiolamides

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Nov. 22, 2024

Language: Английский

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Silver-Catalyzed Dearomative [3+2] Spiroannulation of Aryl Oxamic Acids with Alkynes

Synthesis, Journal Year: 2024, Volume and Issue: 56(20), P. 3191 - 3198

Published: July 3, 2024

Abstract A silver-catalyzed dearomative decarboxylative [3+2] spiroannulation of aryl oxamic acids with alkynes is described. The reaction provides reliable access to a range azaspiro[4,5]trienones in moderate yields aqueous media. In addition, the exhibits broad substrate scope and good functional group compatibility.

Language: Английский

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Synthesis of succinyldiamides containing all-quaternary carbon center by photo-induced amidation/smiles rearrangement of alkenes

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 23, 2024

A novel, mild, and environmentally friendly method was developed for the synthesis of quaternary-carbon-containing succinyldiamides. This found to be compatible with many substrates.

Language: Английский

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