Regioselective palladium-catalyzed decarboxylative cross-coupling reaction of alkenyl acids with coumarins: synthesis of 3-styrylcoumarin compounds.

J Org Chem

Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), School of Chemistry & Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, People's Republic of China.

Published: February 2015

A novel and efficient protocol for the regioselective synthesis of 3-styrylcoumarins from readily available cinnamic acids and coumarins is presented. The reaction proceeds via a decarboxylative cross-coupling mediated by a catalytic amount of Pd(OAc)2, with Ag2CO3 as an oxidant, and with 1,10-phenanthroline as a ligand. A plausible reaction mechanism for this process is depicted, and the resulting 3-styrylcoumarins show excellent fluorescence quantum yields.

Download full-text PDF

Source
http://dx.doi.org/10.1021/jo502572jDOI Listing

Publication Analysis

Top Keywords

decarboxylative cross-coupling
8
acids coumarins
8
regioselective palladium-catalyzed
4
palladium-catalyzed decarboxylative
4
cross-coupling reaction
4
reaction alkenyl
4
alkenyl acids
4
coumarins synthesis
4
synthesis 3-styrylcoumarin
4
3-styrylcoumarin compounds
4

Similar Publications

Article Synopsis
  • The study presents a method using TMSOTf to create spiroketal derivatives through hydroalkoxylation and cycloaddition reactions involving hydroxy cyclopropenes and aldehydes.
  • This process generates a donor-acceptor cyclopropane intermediate, allowing for the efficient synthesis of [5.5]- and [6.5]-spiroketals.
  • The resulting spirocyclic compounds can be further modified to produce complex polycyclic heterocycles through metal halogen exchange and copper-catalyzed reactions, with a decarboxylation step that introduces a fourth chiral center.
View Article and Find Full Text PDF

Enamides have emerged as robust alternatives for enamines, exhibiting versatile reactivity for further synthetic modifications, including nucleophilic addition, cycloaddition, and asymmetric hydrogenation. While transition-metal-catalyzed cross-coupling of alkenyl (pseudo)halides with amides has been widely employed to construct this valuable scaffold, it suffers from some limitations, such as the need for transition-metal catalysts and the preparative synthesis of alkenyl (pseudo)halides. In this study, we report a mild and convenient stereoretentive decarboxylative amidation of α,β-unsaturated carboxylic acids with easily procurable 1,4,2-dioxazol-5-ones, providing a practical synthetic route to enamides.

View Article and Find Full Text PDF

A practical nickel-catalyzed decarboxylative cross-coupling of -hydroxyphthalimide esters with 1,4-diiodobenzene analogues has been developed. Under mild reaction conditions, a series of structurally interesting 1,4-dialkylbenzene analogues have been accessed with good functional group tolerance, which are versatile precursors for organic synthesis and a kind of important unit for bioactive molecules, polymers, and other materials. The synthetic application of this methodology was demonstrated by the synthesis of 3-6-dialkylcarbazole derivatives.

View Article and Find Full Text PDF

An easily accessible Cu(I)-catalyzed regioselective oxidative C-N/C-O cross-coupling organic transformation has been disclosed for the syntheses of variably functionalized triazines and N-benzoylpyrrolidin-2-ones through the involvement of C(sp)-H bond functionalization, which is unknown in the literature. This general synthetic method is extended for decarboxylative oxidation of amino acids to install carbonyl functionality. It facilitates the formation of 2-3 new bonds through the cross-coupling strategy involving benzimidates, amino acids, and in situ-generated reactive oxygen species (ROS) from the aerial O as the sole oxidant.

View Article and Find Full Text PDF

Photocatalytic Decarboxylative Cross-Coupling of α,β-Unsaturated Acids with Amines for α-Ketoamides via C-N Bond Formation.

J Org Chem

November 2024

School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Kolkata 700032, West Bengal, India.

An unprecedented oxidative decarboxylative chemical domain of α,β-unsaturated acids and amines for C-N cross-coupled α-ketoamidation is disclosed. Molecular oxygen as a source oxygen in amide and water oxygen in the ketone segment furnished a green and sustainable synthesis of α-ketoamide from feedstock acids and amines. Mechanistically, photocatalyst travels with reductive quenching cycle, whereas pallado-cycle proceeded through oxidative C-N bond formation.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!