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Base‐free Suzuki‐Miyaura Coupling of ( Z )‐Trifluoromethyl Alkenyltriflates: An Efficient Approach to α ‐Trifluoromethyl Arylenes
Author(s) -
Zhang Chunxia,
Li Dong,
Zhao Yilong,
Zhao Jinfeng,
Qu Jingping,
Zhou Yuhan
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202004030
Subject(s) - trifluoromethyl , chemistry , aryl , base (topology) , catalysis , palladium , bromide , fluoride , medicinal chemistry , coupling reaction , chloride , organic chemistry , alkyl , inorganic chemistry , mathematics , mathematical analysis
An exogenous base is generally necessary for the traditional palladium‐catalyzed Suzuki‐Miyaura coupling reactions. We report a direct palladium‐catalyzed base‐free Suzuki‐Miyaura coupling reaction of α ‐trifluoromethyl alkenyl triflates and aryl boric acids. Using Pd(OAc) 2 (10 mol %) and PPh 3 (40 mol %) as catalyst, this reaction proceeds smoothly without base or other additive. A variety of common functional groups, such as methyl, phenyl, naphthyl, fluoride, chloride, bromide, cyano, thienyl and alkyl, were well tolerated and a series of α ‐trifluoromethyl arylenes were obtained in 84 %–100 % yields.