An improved, efficient route to 2,2-difluoroethenylbenzenes

作者：Lu Long; Burton Donald J^*

来源：Journal of Fluorine Chemistry, 2012, 133: 16-19.

DOI：10.1016/j.jfluchem.2011.06.005

• 2,2-Difluoroethenyltributylstannane
• Pd(PPh3)(4)
• Cu(I)I
• Co-catalysis
• 2,2-Difluoroethenyllithium
• Vinylidene fluoride
• Coupling reactions
• 2,2-Difluorostyrenes

Treatment of vinylidene fluoride with tert-BuLi at - 115 degrees C gave a solution of [F2C=CHLi]. Addition of Bu3SnCl to this lithium reagent at - 110 degrees C gave an 88% isolated yield of F2C=CHSnBu3. Reaction of F2C=CHSnBu3 with substituted aryl iodides under Stille-Liebeskind conditions [Pd(PPh3)(4)/Cu(I)I] at room temperature afforded the 2,2-difluoroethenylbenzines in good yield. In the absence of the Cu(I)I co-catalyst, no reaction occurred. This work provides the most efficient route for the conversion of aryl halides to 2,2-difluorostyrenes.

• 出版日期2012-1