Consecutive cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate with boronic acids: efficient synthesis of 1,1-diaryl-2,2-difluoroethenes

• Ju Hee Kim,
• Su Jeong Choi and
• In Howa Jeong

Beilstein J. Org. Chem. 2013, 9, 2470–2475, doi:10.3762/bjoc.9.286

• yields. Unsymmetrical di-coupled products 4 were obtained in high yields from the reactions of 3 with 2 equiv of boronic acids in the presence of catalytic amounts of Pd(OAc)2 and Na2CO3. Keywords: boronic acids; cross-coupling reaction; 1,1-diaryl-2,2-difluoroethene; 1,1-difluoro-1,3-dienes; 2,2

• 3a with 2 equiv of p-chlorophenylboronic acid in the presence of 5 mol % Pd(PPh3)2Cl2 and 2 equiv of Cs2CO3 in MeOH at room temperature for 12 h afforded 1,1-diaryl-2,2-difluoroethene 4o in 89% yield. The similar reactions of 3a with arylboronic acids having a substituent such as fluoro, methyl