Xiaochen Wang, Senhui Wu, Hongyu Zhang, Qingmin Wang, Shu-Rong Ban
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Combined Photoredox and Carbene Catalysis: Alkene Borocarbonylation via the Persistent Radical Effect
Herein, we report a mild and operationally simple dual-catalytic method for the synthesis of β-boryl carbonyl compounds via alkene difunctionalization. Specifically, combining N-heterocyclic carbene catalysis and photocatalysis enables a three-component radical cross-coupling reaction between a wide range of feedstock carboxylic acids, easily prepared NHC-boranes, and readily available alkenes to yield structurally diverse β-boryl carbonyl compounds. Longer lifetime ketyl radicals facilitate efficient boron participation in the coupling through the persistent radical effect. The method could be used to install acyl and borane groups on highly functionalized natural-product-derived compounds without pre–activation in one step and most products show good diastereoselectivity.
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.