Organophotoredox-Catalyzed Intermolecular Formal Grob Fragmentation of Cyclic Alcohols with Activated Allylic Acetates

Wubing Zeng; Xiaoyu Zhang; Yinlei Zhang; Shiji Xiao; Yongming Tang; Peizhong Xie; Teck Peng Loh

doi:10.1021/acs.orglett.3c02129

Organophotoredox-Catalyzed Intermolecular Formal Grob Fragmentation of Cyclic Alcohols with Activated Allylic Acetates

Wubing Zeng, Xiaoyu Zhang, Yinlei Zhang, Shiji Xiao, Yongming Tang, Peizhong Xie^*, Teck Peng Loh^*

^*Corresponding author for this work

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

6 Citations (Scopus)

Abstract

We have developed an efficient method that employs organophotoredox-catalyzed relay Grob fragmentation to facilitate the smooth ring-opening allylation of cyclic alcohols in an environmentally friendly manner. This protocol directly incorporates a wide spectrum of cyclic alcohols and activated allylic acetates into the cross-coupling reaction, eliminating the need for metal catalysts. The process yields a variety of distally unsaturated ketones with good to excellent outcomes and stereoselectivity, while acetic acid is the sole byproduct.

Original language	English
Pages (from-to)	5869-5874
Number of pages	6
Journal	Organic Letters
Volume	25
Issue number	31
DOIs	https://doi.org/10.1021/acs.orglett.3c02129
Publication status	Published - Aug 11 2023
Externally published	Yes

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Publisher Copyright:
© 2023 American Chemical Society

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.3c02129

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title = "Organophotoredox-Catalyzed Intermolecular Formal Grob Fragmentation of Cyclic Alcohols with Activated Allylic Acetates",

abstract = "We have developed an efficient method that employs organophotoredox-catalyzed relay Grob fragmentation to facilitate the smooth ring-opening allylation of cyclic alcohols in an environmentally friendly manner. This protocol directly incorporates a wide spectrum of cyclic alcohols and activated allylic acetates into the cross-coupling reaction, eliminating the need for metal catalysts. The process yields a variety of distally unsaturated ketones with good to excellent outcomes and stereoselectivity, while acetic acid is the sole byproduct.",

author = "Wubing Zeng and Xiaoyu Zhang and Yinlei Zhang and Shiji Xiao and Yongming Tang and Peizhong Xie and Loh, {Teck Peng}",

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doi = "10.1021/acs.orglett.3c02129",

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T1 - Organophotoredox-Catalyzed Intermolecular Formal Grob Fragmentation of Cyclic Alcohols with Activated Allylic Acetates

AU - Zeng, Wubing

AU - Zhang, Xiaoyu

AU - Zhang, Yinlei

AU - Xiao, Shiji

AU - Tang, Yongming

AU - Xie, Peizhong

AU - Loh, Teck Peng

PY - 2023/8/11

Y1 - 2023/8/11

N2 - We have developed an efficient method that employs organophotoredox-catalyzed relay Grob fragmentation to facilitate the smooth ring-opening allylation of cyclic alcohols in an environmentally friendly manner. This protocol directly incorporates a wide spectrum of cyclic alcohols and activated allylic acetates into the cross-coupling reaction, eliminating the need for metal catalysts. The process yields a variety of distally unsaturated ketones with good to excellent outcomes and stereoselectivity, while acetic acid is the sole byproduct.

AB - We have developed an efficient method that employs organophotoredox-catalyzed relay Grob fragmentation to facilitate the smooth ring-opening allylation of cyclic alcohols in an environmentally friendly manner. This protocol directly incorporates a wide spectrum of cyclic alcohols and activated allylic acetates into the cross-coupling reaction, eliminating the need for metal catalysts. The process yields a variety of distally unsaturated ketones with good to excellent outcomes and stereoselectivity, while acetic acid is the sole byproduct.

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SN - 1523-7060

VL - 25

SP - 5869

EP - 5874

JO - Organic Letters

JF - Organic Letters

IS - 31

ER -

Organophotoredox-Catalyzed Intermolecular Formal Grob Fragmentation of Cyclic Alcohols with Activated Allylic Acetates

Abstract

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ASJC Scopus Subject Areas

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