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A general protocol for radical anion [3 + 2] cycloaddition enabled by tandem Lewis acid photoredox catalysis.


ABSTRACT: We report herein a method for intermolecular [3 + 2] cycloaddition between aryl cyclopropyl ketones and alkenes involving the combination of Lewis acid and photoredox catalysis. In contrast to other more common methods for [3 + 2] cycloaddition, these conditions operate using a broad range of both electron-rich and electron-deficient reaction partners. The critical factors predicting the success of these reactions is the redox potential of the cyclopropyl ketone and the ability of the alkene to stabilize a key radical intermediate.

SUBMITTER: Amador AG 

PROVIDER: S-EPMC5858716 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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A general protocol for radical anion [3 + 2] cycloaddition enabled by tandem Lewis acid photoredox catalysis.

Amador Adrian G AG   Sherbrook Evan M EM   Lu Zhan Z   Yoon Tehshik P TP  

Synthesis 20171019 3


We report herein a method for intermolecular [3 + 2] cycloaddition between aryl cyclopropyl ketones and alkenes involving the combination of Lewis acid and photoredox catalysis. In contrast to other more common methods for [3 + 2] cycloaddition, these conditions operate using a broad range of both electron-rich and electron-deficient reaction partners. The critical factors predicting the success of these reactions is the redox potential of the cyclopropyl ketone and the ability of the alkene to  ...[more]

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