The Suzuki–Miyaura Coupling of Nitroarenes

Yoshiaki Nakao and Shigeyoshi Sakaki report the Suzuki–Miyaura coupling of nitroarenes.

The Suzuki–Miyaura cross-coupling reaction is an indispensable synthetic tool for modern organic synthesis to assemble biaryls, which are ubiquitous in useful substances such as pharmaceuticals, agrochemicals, and materials. One avenue of ongoing research to improve the practicality of the transformation is to seek aryl electrophiles alternative to aryl halides to avoid halogen contaminations in products and wastes as well as to streamline and diversify chemical processes to access biaryls. While many different aryl electrophiles such as aryl esters, aryl ethers, aryl carboxylic acid derivatives, and aryl ammonium salts have been introduced for the Suzuki–Miyaura cross-coupling in the last decade, no successful report has been available for the use of nitroarenes as the coupling partner.

Recently, a research endeavor led by Professor Shigeyoshi Sakaki (Fukui Institute for Fundamental Chemistry, Kyoto University, Japan) and Professor Yoshiaki Nakao (Kyoto University, Japan) showed for the first time that nitroarenes can be viable aryl electrophiles for the Suzuki–Miyaura cross-coupling reaction.

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