A General Protocol for Radical Anion [3+2] Cycloaddition Enabled by Tandem Lewis Acid Photoredox Catalysis

Adrian G. Amador; Evan M. Sherbrook; Zhan Lu; Tehshik P. Yoon

doi:10.1055/s-0036-1591500

A General Protocol for Radical Anion [3+2] Cycloaddition Enabled by Tandem Lewis Acid Photoredox Catalysis

Adrian G. Amador, Evan M. Sherbrook, Zhan Lu, Tehshik P. Yoon

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

Abstract

A method for intermolecular [3+2] cycloaddition between aryl cyclopropyl ketones and alkenes involving the combination of Lewis acid and photoredox catalysis is reported. 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.

Original language	English (US)
Article number	ss-2017-m0573-op
Pages (from-to)	539-547
Number of pages	9
Journal	Synthesis (Germany)
Volume	50
Issue number	3
DOIs	https://doi.org/10.1055/s-0036-1591500
State	Published - Feb 1 2018

Bibliographical note

Funding Information:
This work was conducted using funding from the NIH (GM095666). The mass spectroscopy facilities at UW-Madison are funded in part

Keywords

cycloaddition
cyclopentane
cyclopropane
photocatalysis
photoredox

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10.1055/s-0036-1591500

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5858716

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AU - Yoon, Tehshik P.

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AB - A method for intermolecular [3+2] cycloaddition between aryl cyclopropyl ketones and alkenes involving the combination of Lewis acid and photoredox catalysis is reported. 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.

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KW - cyclopropane

KW - photocatalysis

KW - photoredox

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A General Protocol for Radical Anion [3+2] Cycloaddition Enabled by Tandem Lewis Acid Photoredox Catalysis

Abstract

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Keywords

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