Identification of a Surprising Boronic Acid Homocoupling Process in Suzuki-Miyaura Cross-Coupling Reactions Utilizing a Hindered Fluorinated Arene

• Published in: Synlett Vol. 32; no. 5; pp. 511 - 516
• Main Authors: Gargaro, Samantha L., Dunson, Bre'Shon, Sieber, Joshua D.
• Format: Journal Article
• Language: English
• Published: STUTTGART Thieme Medical Publishers 17.03.2021
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; palladium catalysis; DESIGN; COMPLEXES; CATALYST; BASE; MILD; arylboronic acids; cross-coupling; CHEMISTRY; COMPUTATIONAL CHARACTERIZATION; bromobistrifluoromethylbenzene; TRANSMETALATION PROCESS; Suzuki-Miyaura reaction

The Suzuki-Miyaura cross-coupling reaction of 2-bromo-1,3-bis(trifluoromethyl)benzene with arylboronic acids was evaluated and determined to suffer from the formation of large amounts of boronic acid homocoupling products in conjunction with dehalogenation. Homocoupling product formation in this pro...