As noncovalent chalcogen-bonding interaction is comparatively weak, it remains a true challenge to implement chalcogen-bonding catalysis in an efficient manner. We herein show that a chalcogen-bonding catalysis approach to cyanosilylation of a broad range of ketones can be achieved even using as low as parts per million (ppm) level catalyst loading while the reactions were completed within several minutes at room temperature. Considering the nature of weak noncovalent forces, this chalcogen-bonding catalysis approach is remarkable as it can give up to 10 6 /h turnover frequency numbers.
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.
As noncovalent chalcogen‐bonding interaction is comparatively weak, it remains a true challenge to implement chalcogen‐bonding catalysis in an efficient manner. Enabled by a class of extraordinary catalysts, it was demonstrated that a dual chalcogen‐bonding catalysis approach to the cyanosilylation of ketones can be achieved even using as low as ppm‐level catalyst loading while the reactions were completed within several minutes. This extremely efficient catalysis approach shows the unique advantage of chalcogen‐bonding interactions and demonstrates the potential of this catalysis concept. More information can be found in the Communication by Yao Wang et al.
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