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Synlett 1992; 1992(3): 207-210
DOI: 10.1055/s-1992-21315
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Synthesis of Sterically Hindered Biaryls via the Palladium-Catalyzed Cross-Coupling Reaction of Arylboronic Acids or their Esters with Haloarenes

Takeo Watanabe* , Norio Miyaura, Akira Suzuki
  • *Department of Applied Chemistry, Faculty of Engineering, Hokkaido University, Sapporo 060, Japan
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Publication Date:
08 March 2002 (online)

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Sterically hindered arylboronic acids such as mesitylboronic acid (1a) were cross-coupled with 2-substituted haloarenes in high yields in the presence of tetrakis(triphenyl-phosphine)palladium(0) and aqueous barium hydroxide in 1,2-dimethoxyethane. An alternative procedure using esters of boronic acids and tripotassium phosphate in dimethylformamide was also newly developed for the cross-coupling reaction of arylboronic acids which are sensitive to hydrolytic deboronation with aqueous base.