Regioselective Synthesis of Fused Furans by Decarboxylative Annulation of α,β‐Alkenyl Carboxylic Acid with Cyclic Ketone: Synthesis of Di‐Heteroaryl Derivatives

Agasti, Soumitra; Pal, Tapas; Achar, Tapas Kumar; Maiti, Sukumar; Pal, Debasis; Mandal, Smita; Daud, Kishan; Lahiri, Goutam Kumar

doi:10.1002/ange.201906264

Cited by 8 publications

(1 citation statement)

References 90 publications

(14 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…reported a new copper‐mediated cyclization reaction of cyclic ketones with α , β ‐alkenyl carboxylic acids to access precious di ‐heterocycles (Scheme 12). [25] The cyclization process could be tolerated for various aliphatic ketones 72 and heterocyclic alkenyl carboxylic acids 73 , generating substituted furan derivatives 74 with high regioselectivity. Notably, increasing the ring size of ketone partners to a 15‐membered ring did not affect the reaction, illustrating the generality of the current procedure.…”

Section: Metal‐catalyzed Decarboxylative Cyclizationmentioning

confidence: 99%

Heterocycle Synthesis via Decarboxylative Cyclization Methods

Wang

Qiu

et al. 2022

Adv Synth Catal

View full text Add to dashboard Cite

Carboxylic acid compounds are important structural units that exist widely in nature; the only byproduct in the decarboxylation process is carbon dioxide, which is non‐flammable, non‐toxic, and easy to remove. Therefore, decarboxylative reactions are of great importance in synthetic chemistry. Heterocyclic compounds are important backbones that constitute a variety of biologically active molecules; therefore, research into the development of new synthetic tactics for heterocyclic derivatives based on decarboxylative cyclization is of great interest. In this paper, we describe metal‐catalyzed, visible light‐driven, electrochemically enabled, decarboxylative cyclization reactions, as well as other types, that have been rapidly developed in the past five years; moreover, for some of these methods, we discuss the scope of their application and the mechanism of the reaction.

show abstract

Section: Metal‐catalyzed Decarboxylative Cyclizationmentioning

confidence: 99%

Heterocycle Synthesis via Decarboxylative Cyclization Methods

Wang

Qiu

et al. 2022

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

Utilization of C(sp³)‐Carboxylic Acids and Their Redox‐Active Esters in Decarboxylative Carbon−Carbon Bond Formation

et al. 2021

View full text Add to dashboard Cite

Over the last several years, radical‐mediated decarboxylative cross‐coupling reactions employing alkyl carboxylic acids have emerged as a powerful tool for the regiospecific construction of carbon−carbon bonds. Under thermal or photocatalytic conditions, a wide variety of C(sp3)‐carboxylic acids and their redox‐active esters undergo decarboxylative C−C bond formation with suitable reactant partners, leading to complex chemical scaffolds with wide‐ranging applications. This synthetic strategy has several advantages over the more conventional organometallic reagents, including abundant starting material availability and high functional group tolerance associated with the mild reaction conditions. This review article highlights recent developments in the functionalization of α‐heteroatom‐substituted carboxylic acids as well as the more challenging unactivated acids, with representative examples discussed against the backdrop of insightful comments on reaction mechanisms. In addition, examples of the synthesis of natural products, drug molecules, and the late‐stage modification of bioactive molecules employing this non‐traditional C−C bond formation strategy are included. This review has been categorized into three main sections that are organized around the type of C−C bond being forged: C(sp3)−C(sp2), C(sp3)−C(sp3), and C(sp3)−C(sp). Further, the reactions of carboxylic acids and their redox‐active esters have been organized separately in each section.

show abstract

Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C‐O/C‐H Coupling

Liu

Zhou

et al. 2021

Angewandte Chemie

View full text Add to dashboard Cite

Cooperative bimetallic catalysis is a fundamental approach in modern synthetic chemistry. We report bimetallic cooperative catalysis for the direct decarbonylative heteroarylation of ubiquitous carboxylic acids via acyl C‐O/C‐H coupling. This novel catalytic system exploits the cooperative action of a copper catalyst and a palladium catalyst in decarbonylation, which enables highly chemoselective synthesis of important heterobiaryl motifs through the coupling of carboxylic acids with heteroarenes in the absence of prefunctionalization or directing groups. This cooperative decarbonylative method uses common carboxylic acids and shows a remarkably broad substrate scope (>70 examples), including late‐stage modification of pharmaceuticals and streamlined synthesis of bioactive agents. Extensive mechanistic and computational studies were conducted to gain insight into the mechanism of the reaction. The key step involves intersection of the two catalytic cycles via transmetallation of the copper–aryl species with the palladium(II) intermediate generated by oxidative addition/decarbonylation.

show abstract

Regioselective Synthesis of Fused Furans by Decarboxylative Annulation of α,β‐Alkenyl Carboxylic Acid with Cyclic Ketone: Synthesis of Di‐Heteroaryl Derivatives

Cited by 8 publications

References 90 publications

Heterocycle Synthesis via Decarboxylative Cyclization Methods

Heterocycle Synthesis via Decarboxylative Cyclization Methods

Utilization of C(sp³)‐Carboxylic Acids and Their Redox‐Active Esters in Decarboxylative Carbon−Carbon Bond Formation

Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C‐O/C‐H Coupling

Contact Info

Product

Resources

About

Regioselective Synthesis of Fused Furans by Decarboxylative Annulation of α,β‐Alkenyl Carboxylic Acid with Cyclic Ketone: Synthesis of Di‐Heteroaryl Derivatives

Cited by 8 publications

References 90 publications

Heterocycle Synthesis via Decarboxylative Cyclization Methods

Heterocycle Synthesis via Decarboxylative Cyclization Methods

Utilization of C(sp3)‐Carboxylic Acids and Their Redox‐Active Esters in Decarboxylative Carbon−Carbon Bond Formation

Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C‐O/C‐H Coupling

Contact Info

Product

Resources

About

Utilization of C(sp³)‐Carboxylic Acids and Their Redox‐Active Esters in Decarboxylative Carbon−Carbon Bond Formation