Abstract:
Dihydrobenzofuran is an important skeleton for bioactive compounds and natural products. Hydroquinones can be easily modified into substituted hydroquinones, which effectively undergo oxidation to produce the corresponding benzoquinone derivatives. Benzoquinones are reactive electrophiles that are frequently utilized in coupling with olefins to dihydrobenzofurans. Herein, we report the one-pot oxidative coupling of hydroquinones bearing an electron-withdrawing group at the C2 position with olefins to dihydrobenzofurans in the presence of the Lewis acidic FeCl3 and 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) oxidant. Furthermore, this method was applied to the oxidative coupling of N-electron-withdrawing group-substituted 4-aminophenol.
摘要:
二氢苯并呋喃是生物活性化合物和自然产品的重要骨架。氢醌可以很容易地修饰成取代的氢醌,其有效地经历氧化以产生相应的苯醌衍生物。苯醌是反应性亲电子试剂,其经常用于与烯烃偶联至二氢苯并呋喃。在这里,我们报道了在路易斯酸FeCl3和2,3-二氯-5,6-二氰基-对苯醌存在下,在C2位置带有吸电子基团的氢醌与烯烃的一锅法氧化偶联为二氢苯并呋喃(DDQ)氧化剂。此外,该方法适用于N-吸电子基团取代的4-氨基苯酚的氧化偶联。