Unexpected Intermolecular Pd-Catalyzed Cross-Coupling Reaction Employing Heteroaromatic Carboxylic Acids as Coupling Partners.

AbstractDiflunisal and Felbinac, two FDA-approved NSAIDs and other biphenyl carboxylic acids were prepared in one step by a simple and clean Suzuki cross-coupling reaction using an easily synthesized, air and moisture stable, palladium-diamine complex. The yield (93%) for the one-step preparation of Diflunisal is the best reported without using a glovebox and a phoshine-based catalyst.

Download Full-text

Palladium-Catalyzed Decarboxylative Cross-Coupling Reaction Between Heteroaromatic Carboxylic Acids and Aryl Halides

The Journal of Organic Chemistry ◽

10.1021/jo9022793 ◽

2010 ◽

Vol 75 (5) ◽

pp. 1550-1560 ◽

Cited By ~ 114

Author(s):

François Bilodeau ◽

Marie-Christine Brochu ◽

Nicolas Guimond ◽

Kris H. Thesen ◽

Pat Forgione

Keyword(s):

Carboxylic Acids ◽

Coupling Reaction ◽

Cross Coupling ◽

Aryl Halides ◽

Cross Coupling Reaction ◽

Palladium Catalyzed

Download Full-text

Unexpected Intermolecular Pd-Catalyzed Cross-Coupling Reaction Employing Heteroaromatic Carboxylic Acids as Coupling Partners

Journal of the American Chemical Society ◽

10.1021/ja063511f ◽

2006 ◽

Vol 128 (35) ◽

pp. 11350-11351 ◽

Cited By ~ 290

Author(s):

Pat Forgione ◽

Marie-Christine Brochu ◽

Miguel St-Onge ◽

Kris H. Thesen ◽

Murray D. Bailey ◽

...

Keyword(s):

Carboxylic Acids ◽

Coupling Reaction ◽

Cross Coupling ◽

Cross Coupling Reaction

Download Full-text

Asymmetric benzylic C(sp3)−H acylation via dual nickel and photoredox catalysis

Nature Communications ◽

10.1038/s41467-021-23887-2 ◽

2021 ◽

Vol 12 (1) ◽

Author(s):

Leitao Huan ◽

Xiaomin Shu ◽

Weisai Zu ◽

De Zhong ◽

Haohua Huo

Keyword(s):

Carboxylic Acids ◽

Organic Synthesis ◽

Late Stage ◽

Coupling Reaction ◽

Cross Coupling ◽

Photoredox Catalysis ◽

Mechanistic Studies ◽

Cross Coupling Reaction ◽

Aryl Ketones ◽

Alkyl Benzenes

AbstractAsymmetric C(sp3)−H functionalization is a persistent challenge in organic synthesis. Here, we report an asymmetric benzylic C−H acylation of alkylarenes employing carboxylic acids as acyl surrogates for the synthesis of α-aryl ketones via nickel and photoredox dual catalysis. This mild yet straightforward protocol transforms a diverse array of feedstock carboxylic acids and simple alkyl benzenes into highly valuable α-aryl ketones with high enantioselectivities. The utility of this method is showcased in the gram-scale synthesis and late-stage modification of medicinally relevant molecules. Mechanistic studies suggest a photocatalytically generated bromine radical can perform benzylic C−H cleavage to activate alkylarenes as nucleophilic coupling partners which can then engage in a nickel-catalyzed asymmetric acyl cross-coupling reaction. This bromine-radical-mediated C−H activation strategy can be also applied to the enantioselective coupling of alkylarenes with chloroformate for the synthesis of chiral α-aryl esters.

Download Full-text

ChemInform Abstract: Palladium-Catalyzed Decarboxylative Cross-Coupling Reaction Between Heteroaromatic Carboxylic Acids and Aryl Halides.

ChemInform ◽

10.1002/chin.201024088 ◽

2010 ◽

Vol 41 (24) ◽

pp. no-no

Author(s):

Francois Bilodeau ◽

Marie-Christine Brochu ◽

Nicolas Guimond ◽

Kris H. Thesen ◽

Pat Forgione

Keyword(s):

Carboxylic Acids ◽

Coupling Reaction ◽

Cross Coupling ◽

Aryl Halides ◽

Cross Coupling Reaction ◽

Palladium Catalyzed

Download Full-text

Copper-catalyzed oxidative coupling of arylboronic acids with aryl carboxylic acids: Cu3(BTC)2 MOF as a sustainable catalyst to access aryl esters

Organic Chemistry Frontiers ◽

10.1039/c8qo00519b ◽

2018 ◽

Vol 5 (15) ◽

pp. 2322-2331 ◽

Cited By ~ 10

Author(s):

Nainamalai Devarajan ◽

Palaniswamy Suresh

Keyword(s):

Carboxylic Acids ◽

Oxidative Coupling ◽

Metal Organic Framework ◽

Coupling Reaction ◽

Cross Coupling ◽

Arylboronic Acids ◽

Cross Coupling Reaction ◽

Metal Organic ◽

Commercially Important ◽

Organic Framework

A straightforward and sustainable methodology for the synthesis of commercially important aryl esters via a C–O cross-coupling reaction was demonstrated using the Cu3(BTC)2 metal–organic framework.

Download Full-text