Lumiflavine-catalyzed, visible-light-driven allylation of cyclobutanone oximes: a sustainable approach to distally unsaturated nitriles

Yanyu Lu; Kaiyu Yan; Yanzhe Shi; Cuiqing Gao; Yitao Zhu; Yinlei Zhang; Teck Peng Loh; Peizhong Xie

doi:10.1039/d5qo00695c

Lumiflavine-catalyzed, visible-light-driven allylation of cyclobutanone oximes: a sustainable approach to distally unsaturated nitriles

Yanyu Lu, Kaiyu Yan, Yanzhe Shi, Cuiqing Gao, Yitao Zhu, Yinlei Zhang, Teck Peng Loh, Peizhong Xie^*

^*Corresponding author for this work

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

Abstract

We present a naturally derived organophotoredox catalyst system for the ring-opening allylation of cyclobutanone O-acetyl oxime esters. This metal-free process operates under mild and environmentally benign conditions, demonstrating broad substrate compatibility. A range of distally unsaturated nitriles was synthesized in good to excellent yields with high stereoselectivity.

Original language	English
Journal	Organic Chemistry Frontiers
DOIs	https://doi.org/10.1039/d5qo00695c
Publication status	Accepted/In press - 2025
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2025 The Royal Society of Chemistry.

ASJC Scopus Subject Areas

Organic Chemistry

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10.1039/d5qo00695c

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title = "Lumiflavine-catalyzed, visible-light-driven allylation of cyclobutanone oximes: a sustainable approach to distally unsaturated nitriles",

abstract = "We present a naturally derived organophotoredox catalyst system for the ring-opening allylation of cyclobutanone O-acetyl oxime esters. This metal-free process operates under mild and environmentally benign conditions, demonstrating broad substrate compatibility. A range of distally unsaturated nitriles was synthesized in good to excellent yields with high stereoselectivity.",

author = "Yanyu Lu and Kaiyu Yan and Yanzhe Shi and Cuiqing Gao and Yitao Zhu and Yinlei Zhang and Loh, \{Teck Peng\} and Peizhong Xie",

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year = "2025",

doi = "10.1039/d5qo00695c",

language = "English",

journal = "Organic Chemistry Frontiers",

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T1 - Lumiflavine-catalyzed, visible-light-driven allylation of cyclobutanone oximes

T2 - a sustainable approach to distally unsaturated nitriles

AU - Lu, Yanyu

AU - Yan, Kaiyu

AU - Shi, Yanzhe

AU - Gao, Cuiqing

AU - Zhu, Yitao

AU - Zhang, Yinlei

AU - Loh, Teck Peng

AU - Xie, Peizhong

PY - 2025

Y1 - 2025

N2 - We present a naturally derived organophotoredox catalyst system for the ring-opening allylation of cyclobutanone O-acetyl oxime esters. This metal-free process operates under mild and environmentally benign conditions, demonstrating broad substrate compatibility. A range of distally unsaturated nitriles was synthesized in good to excellent yields with high stereoselectivity.

AB - We present a naturally derived organophotoredox catalyst system for the ring-opening allylation of cyclobutanone O-acetyl oxime esters. This metal-free process operates under mild and environmentally benign conditions, demonstrating broad substrate compatibility. A range of distally unsaturated nitriles was synthesized in good to excellent yields with high stereoselectivity.

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U2 - 10.1039/d5qo00695c

DO - 10.1039/d5qo00695c

M3 - Article

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JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

ER -

Lumiflavine-catalyzed, visible-light-driven allylation of cyclobutanone oximes: a sustainable approach to distally unsaturated nitriles

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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