Palladium catalyzed oxidation of biorenewable β-citronellol and geraniol for the synthesis of polyfunctionalized fragrances
作者:Aldino N. Venancio、Luciano Menini、Daiane N. Maronde、Elena V. Gusevskaya、Luciana A. Parreira
DOI:10.1016/j.mcat.2021.111449
日期:2021.3
plants. Allylic oxidation of trisubstituted sterically highly encumbered carbon-carbon double bonds in their molecules with dioxygen can be efficiently catalyzed by the palladium acetate/p-benzoquinone combination under 5−10 atm of dioxygen pressure without the need for conventionally used metal co-catalysts. Both substrates gave allyl acetates in ca. 90% combined yield. The oxidation of geraniol proceeded
β-香茅醇和香叶醇是在各种植物的精油中发现的可生物再生的化合物。乙酸钯/对苯醌的组合可在5-10 atm的氧气压力下,有效地催化三取代的空间取代分子中高度取代的碳-碳双键在分子中的烯丙基氧化反应,而无需常规使用的金属助催化剂。两种底物在约70℃下均得到乙酸烯丙酯。合并产率为90%。香叶醇的氧化具有出色的位点选择性,仅涉及其两个C之一C键。香叶醇以可比的产率产生直链和支链乙酸烯丙酯,而β-香茅醇的反应对相应的支链产物显示出高区域选择性。由β-香茅醇和香叶醇生产的多官能氧化的萜烯作为香料组合物的成分具有潜在的重要性。