4-METHOXYPHENYL BORONIC ACID

4-METHOXYPHENYL BORONIC ACID

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The heterogeneous palladium-catalyzed Suzuki reactions between model aryl bromides (4-bromoanisole, 4-bromoaniline, 4-amino-2-bromopyridine, and 2-bromopyridine) and phenylboronic acid have been successfully conducted in water with no added ligand at the 100 mL scale using 20–40 mmol of aryl bromide. The product yields associated with these substrates were optimized, and key reaction parameters affecting the yields were identified. The results clearly indicate that the reaction parameters necessary to achieve high yields are substrate-dependent. In addition, it is demonstrated that aqueous Suzuki reactions of substrates containing basic nitrogen centers can produce quantitative yields of desired products in the absence of added ligand.

Palladium-Catalyzed Suzuki Reactions in Water with No Added Ligand: Effects of Reaction Scale, Temperature, pH of Aqueous Phase, and Substrate Structure

Zhao Li^†, Carol Gelbaum^†, William L. HeanerIV^†, Jason Fisk^§, Arvind Jaganathan^§, Bruce Holden^§, Pamela Pollet^†, and Charles L. Liotta^*†‡

^† School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332, United States

^‡ School of Chemical and Biomolecular Engineering, Georgia Institute of Technology, Atlanta, Georgia 30332, United States

^§ The Dow Chemical Company, Midland, Michigan 48674, United States

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/acs.oprd.6b00180

*E-mail: charles.liotta@chemistry.gatech.edu.

http://pubs.acs.org/doi/abs/10.1021/acs.oprd.6b00180

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• Supporting Info

KOLI FOOD, MAHARASHTRA, INDIA














































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