One-Pot Transformation of Salicylaldehydes to Spiroepoxydienones via the Adler-Becker Reaction in a Continuous Flow

ACS Omega. 2022 Mar 31;7(14):11570-11577. doi: 10.1021/acsomega.1c05559. eCollection 2022 Apr 12.

Abstract

The Adler-Becker reaction is a useful approach for the oxidative dearomatization of salicylic alcohols to spiroepoxydienones and has been applied in the total synthesis of several natural products. Despite the advantages, the substrate and product instability under the reaction conditions can decrease the reaction efficiency, leading to lower yields. Herein, we report the Adler-Becker reaction in a continuous flow for the transformation of reduced salicylaldehydes into spiroepoxydienones in a one-pot approach. For that, a heterogeneous oxidant based on periodate is developed, leading to an efficient continuous flow process, with higher productivity and shorter reaction times, when compared with batch conditions.