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Boron-Catalyzed O-H Bond Insertion of α-Aryl α-Diazoesters in Water.

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A catalytic, metal-free O-H bond insertion of α-diazoesters in water in the presence of B(C6F5)3· nH2O (2 mol %) was developed, affording a series of α-hydroxyesters in good to excellent… Click to show full abstract

A catalytic, metal-free O-H bond insertion of α-diazoesters in water in the presence of B(C6F5)3· nH2O (2 mol %) was developed, affording a series of α-hydroxyesters in good to excellent yields. The reaction features easy operation and wide substrate scope, and importantly, no metal is needed as compared with the conventional methods. Significantly, this approach further expands the applications of B(C6F5)3 under water-tolerant conditions.

Keywords: water; bond insertion; boron catalyzed; diazoesters water

Journal Title: Organic letters
Year Published: 2018

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