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Abstract
In recent years, asymmetric electrocatalysis has emerged as a powerful and efficient tool for constructing enantioenriched compounds. However, developing asymmetric transformations using N-heterocyclic carbene (NHC)-catalyzed radical reactions is still very desirable and challenging. Herein, we report an iodide-promoted β-carbon activation of enals via electroredox carbene catalysis coupled with a hydrogen evolution reaction (HER). This strategy offers an environmentally friendly and sustainable route for rapidly assembling synthetically useful chiral naphthopyran-3-one in good to excellent yield and enantioselectivity, using traceless electrons as an inexpensive and greener oxidant. The mechanistic studies and cyclic voltammetry suggest that the reaction proceeds via direct single electron oxidation (SET) of the in-situ Breslow intermediate.
Supplementary materials
Title
Electroredox N-Heterocyclic Carbene-Catalyzed Enantioselective (3+3) Annulation of Enals with 2-Naphthols
Description
In recent years, asymmetric electrocatalysis has emerged as a powerful and efficient tool for constructing enantioenriched compounds. However, developing asymmetric transformations using N-heterocyclic carbene (NHC)-catalyzed radical reactions is still very desirable and challenging. Herein, we report an iodide-promoted β-carbon activation of enals via electroredox carbene catalysis coupled with a hydrogen evolution reaction (HER). This strategy offers an environmentally friendly and sustainable route for rapidly assembling synthetically useful chiral naphthopyran-3-one in good to excellent yield and enantioselectivity, using traceless electrons as an inexpensive and greener oxidant. The mechanistic studies and cyclic voltammetry suggest that the reaction proceeds via direct single electron oxidation (SET) of the in-situ Breslow intermediate.
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