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

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...

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Bibliographic Details
Published inSynlett Vol. 32; no. 5; pp. 511 - 516
Main Authors Gargaro, Samantha L., Dunson, Bre'Shon, Sieber, Joshua D.
Format Journal Article
LanguageEnglish
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
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Summary: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 process likely occurs through a rare protonolysis/second transmetalation event rather than by the well-established mechanism requiring the involvement of O-2. The scope of this boronic acid homocoupling reaction was investigated and shown to predominate with electron-deficient arylboronic acids. Finally, a good yield of cross-coupling products could be obtained by employing dicyclohexyl(2 ',6 '-dimethoxybiphenyl-2-yl)phosphine (SPhos) as the ligand.
Bibliography:Bill and Melinda Gates Foundation
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0040-1707266