School of Chemistry and Chemical Engineering Key Laboratory of the Colloid and Interface Chemistry, Ministry of Education, Shandong University, Jinan, 250100, P. R. China.
Chemistry. 2023 May 8;29(26):e202203822. doi: 10.1002/chem.202203822. Epub 2023 Mar 22.
The Cloke-Wilson rearrangement is an important method to construct heterocycles which was conventionally facilitated by strong Lewis acids, Brønsted acids and Lewis bases. A weak interaction catalysis approach to the Cloke-Wilson rearrangement remains a challenging topic and yet no example is reported. Herein, a chalcogen bonding catalysis method to achieve the Cloke-Wilson rearrangement is described that involves activation of carbonyl cyclopropanes by double Se⋅⋅⋅O interactions. This chalcogen bonding catalysis approach afforded a wide range of dihydrofurans with good yields, thus establishing an alternative strategy to catalyze the Cloke-Wilson rearrangement.
克劳克-威尔森重排是构建杂环的一种重要方法，通常需要使用强路易斯酸、布朗斯特酸和路易斯碱来促进。用弱相互作用催化克劳克-威尔森重排仍然是一个具有挑战性的课题，目前尚无报道。本文描述了一种通过二硒······氧相互作用激活羰基环丙烷来实现克劳克-威尔森重排的硫属键催化方法。这种硫属键催化方法提供了广泛的具有良好收率的二氢呋喃，从而为催化克劳克-威尔森重排提供了一种替代策略。
