Arylboronic acids catalyzed upgrade of glucosamines for deoxyfructosazine and insights on reaction mechanism

Mechanism of arylboronic acid-catalyzed amidation reaction between carboxylic acids and amines.

Arylboronic acids were found to be efficient catalysts for the amidation reactions between carboxylic acids and amines. Theoretical calculations have been carried out to investigate the mechanism of this catalytic process. It is found that the formation of the acyloxyboronic acid intermediates from the carboxylic acid and the arylboronic acid is kinetically facile but thermodynamically unfavora...

Ligand-free Palladium-Catalyzed Mizoroki-Heck-type Reaction of Arylboronic Acids and Alkenes Using Silver Cation

Palladium(II)-catalyzed Heck reaction of aryl halides and arylboronic acids with olefins under mild conditions

A series of general and selective Pd(II)-catalyzed Heck reactions were investigated under mild reaction conditions. The first protocol has been developed employing an imidazole-based secondary phosphine oxide (SPO) ligated palladium complex (6) as a precatalyst. The catalytic coupling of aryl halides and olefins led to the formation of the corresponding coupled products in excellent yields. A v...

Enantioselective rhodium-catalyzed addition of arylboronic acids to trifluoromethyl ketones.

The catalytic asymmetric 1,2-addition of a series of arylboronic acids to 2,2,2-trifluoroacetophenones is described with high isolated yields (up to 96%) and good enantioselectivities (up to 83% ee) using a rhodium(I)/phosphoramidite catalyst.

The coupling of arylboronic acids with nitroarenes catalyzed by rhodium.

The coupling of arylboronic acids with electron-deficient nitroarenes was realized for the first time by using a rhodium(I) catalyst under an air atmosphere, achieving unsymmetrical diaryl ethers with yields ranging from poor to good. From a deuterium labeling experiment, the oxygen atom is derived from ambient water. The efficiency of this reaction was demonstrated by its compatibility with fl...