Palladium-Catalyzed, Direct Boronic Acid Synthesis from Aryl Chlorides: A Simplified Route to Diverse Boronate Ester Derivatives

Gary A. Molander*, Sarah L. J. Trice and Spencer D. Dreher

*Penn/Merck Laboratory for High Throughput Experimentation, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States, Email: gmolandrsas.upenn.edu

G. A. Molander, S. L. J. Trice, S. D. Dreher, J. Am. Chem. Soc., 2010, 132, 17701-17703.

DOI: 10.1021/ja1089759

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Abstract

A simple and efficient palladium-catalyzed reaction of aryl chlorides with tetrahydroxydiboron gives arylboronic acids. To ensure preservation of the carbon-boron bond, the boronic acids were efficiently converted in situ to trifluoroborate derivatives or boronates in very good yields. Finally, a two-step, one-pot method for the synthesis of biaryls from two aryl chlorides was developed.

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Nickel-Catalyzed Borylation of Halides and Pseudohalides with Tetrahydroxydiboron [B₂(OH)₄]

G. A. Molander, L. N. Cavalcanti, C. García-García, J. Org. Chem., 2013, 78, 6427-6439.

Scope of the Two-Step, One-Pot Palladium-Catalyzed Borylation/Suzuki Cross-Coupling Reaction Utilizing Bis-Boronic Acid

G. A. Molander, S. L. J. Trice, S. M. Kennedy, J. Org. Chem., 2012, 77, 8678-8688.

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Key Words

Miyaura Borylation, Aryltrifluoroborates, Suzuki Coupling, Biaryls

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ID: J48-Y2010-3490