A novel and convenient synthetic method for producing α-(trifluoromethyl)styrenes ( 3)

• Published in: Journal of fluorine chemistry Vol. 95; no. 1; pp. 167 - 170
• Main Authors: Pan, Rui-qi, Liu, Xing-xin, Deng, Min-zhi
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 04-06-1999
• Subjects: 1,2-dibromo-3,3,3-trifluoropropane; 2-bromo-trifluoropropene; Arylboronic acid; Suzuki-type coupling; α-(trifluoromethyl)styrenes; 1,2-dibromo-3,3,3-trifluoropropane; Suzuki-type coupling; 2-bromo-trifluoropropene; α-(trifluoromethyl)styrenes; Arylboronic acid
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/S0022-1139(99)00021-4

The Suzuki-type coupling reaction of arylboronic acids (
1) with 2-bromo-3,3,3-trifluoropropene (
2) in the presence of a catalytic amount of dichlorobis(triphenylphosphine)palladium {PdCl
2(PPh
3)
2} and a base can easily give α-(trifluoromethyl)styrenes (
3) in good yields. It was also found that 1,2-dibromo-3,3,3-trifluoropropane (
4) underwent dehydrobromination in the presence of KOH, and subsequently, palladium-catalyzed cross-coupling with
1 to directly afford
3 in a one pot manner in excellent yields.