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Abstract
Herein, we describe the development of a photoredox‐catalyzed decarboxylative radical addition–polar cyclization cascade approach to functionalized cyclopropanes. Reductive termination of radical–polar crossover reactions between aliphatic carboxylic acids and electron‐deficient alkenes yielded carbanion intermediates that were intercepted in intramolecular alkylations with alkyl chlorides appended to the alkene substrate. The mild conditions, which make use of a readily available organic photocatalyst and visible light, were demonstrated to be amenable to a broad range of structurally complex carboxylic acids and a wide variety of chloroalkyl alkenes, demonstrating exquisite functional group tolerance.
Highlights
Over the last decade, photoredox catalysis has been extensively explored.[1]
A single-electron transfer (SET) event leads to a carbocation or a carbanion, which can react with a nucleophile or electrophile, respectively
We queried whether the catalytically-generated carbanions could undergo intramolecular alkylations with alkyl halides, as this would provide a decarboxylative radical addition–polar cyclization cascade for the synthesis of cyclic boronic esters (Scheme 1 B).[8]
Summary
Photoredox catalysis has been extensively explored.[1]. The mild conditions, high functional group tolerance, and diversity of compatible carbon-centered radical precursors, has resulted in numerous synthetically valuable methodologies, in the area of alkene functionalization.[2]. Esters, proceeding through a radical–polar crossover with reductive termination to give an a-boryl anion.[7] We queried whether the catalytically-generated carbanions could undergo intramolecular alkylations with alkyl halides, as this would provide a decarboxylative radical addition–polar cyclization cascade for the synthesis of cyclic boronic esters (Scheme 1 B).[8] We were interested in targeting cyclopropanes, as these strained carbocycles are highly valuable motifs in drug development and are common components of bioactive natural products.[9]
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