Journal of Catalysis ( IF 6.5 ) Pub Date : 2022-06-23 , DOI: 10.1016/j.jcat.2022.06.032 Zhi-Peng Bao , Youcan Zhang , Xiao-Feng Wu
Compared with unactivated alkyl olefins, the corresponding fluorinative carbonylation of styrenes has remained a challenge due to its strong tendency for oligomerization and polymerization. In this communication, we developed a palladium-catalyzed four-component difluoroalkylative carbonylation of aryl olefins for the first time. A wide range of β-difluoromethylene substituted amide derivatives were prepared in moderate to high yields with excellent regioselectivity. Notably, ethylene gas, as an original C2 synthon, can also be transformed to the corresponding products with moderate yields. Furthermore, some natural product or bio-active molecule related compounds, such as estrogen, benzocaine, and menthol derivatives can be reacted as well. This reaction can be scaled up smoothly and the obtained product can be further transformed into amidic acid and aminol efficiently.
中文翻译:
钯催化芳基烯烃和乙烯的四组分二氟烷基羰基化
与未活化的烷基烯烃相比,苯乙烯的相应氟化羰基化由于其强烈的低聚和聚合趋势而一直是一个挑战。在本次交流中,我们首次开发了钯催化的芳基烯烃四组分二氟烷基羰基化反应。β范围广-二氟亚甲基取代的酰胺衍生物以中等至高产率制备,具有优异的区域选择性。值得注意的是,乙烯气体作为原始的 C2 合成子,也可以以中等收率转化为相应的产物。此外,一些天然产物或生物活性分子相关化合物,如雌激素、苯佐卡因和薄荷醇衍生物也可以反应。该反应可以顺利放大,所得产物可以进一步高效转化为酰胺酸和氨基醇。