Chalcogen Bonding Catalysis of the Cloke-Wilson Rearrangement

The Cloke-Wilson rearrangement is an important method to construct heterocycles which was conventionally facilitated by strong Lewis acids, Bronsted 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 SeO 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.

Automated summary

The Cloke-Wilson rearrangement is a significant method for constructing heterocycles, traditionally facilitated by strong Lewis acids, Bronsted acids, and Lewis bases. However, a weak interaction catalysis approach to this rearrangement has remained challenging and unreported. This study presents a chalcogen bonding catalysis method using double SeO interactions to activate carbonyl cyclopropanes and achieve the Cloke-Wilson rearrangement. This alternative strategy successfully yields a wide range of dihydrofurans, providing a new approach for catalyzing the Cloke-Wilson rearrangement.