Chalcogen Bonding Catalysis of the Cloke‐Wilson Rearrangement
Xinglong Yuan, Lintao Bao, Zhiguo Zhao, Yao Wang
Abstract
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.
Topics & Concepts
ChalcogenCatalysisChemistryLewis acids and basesBrønsted–Lowry acid–base theoryStereochemistryComputational chemistryOrganic chemistrySulfur-Based Synthesis TechniquesAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization Methods