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DOI: 10.1055/s-2008-1078437
Cross-Coupling of ArN2BF4 with ArB(OH)2
F.-X. Felpin*, E. Fouquet
Université Bordeaux 1, Talence, France
Publication History
Publication Date:
20 June 2008 (online)
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Significance
The cross-coupling reaction of arenediazonium tetrafluoroborate salts with boronic acids was achieved by using palladium(0)/barium carbonate as a catalyst. The reactions were carried out in the presence of 0.1-2.0 mol% of the catalyst to give the corresponding biaryl compounds in 77-98% yield (12 examples). The authors also reported the synthesis of unsymmetrical terphenyl in a one-pot process. The cross-coupling reaction of 4-iodobenzenediazonium tetrafluoroborate salt with phenyl boronic acid proceeded under base-free conditions to give 4-iodobiphenyl. The subsequent cross-coupling reaction of 4-iodobiphenyl with (3,4-dimethoxyphenyl)boronic acid took place smoothly in refluxing methanol in the presence of aqueous Na2CO3 to afford unsymmetrical terphenyl in 92% yield.