Photoredox Catalyzed Conia-Ene-Type Cyclization/Smiles Rearrangement Cascade Reactions to Access Substituted Methylenecarbocycles

Keyuan Zhang; Qi Jiang; Chonglong He; Mingyou Hu; Yangyang Cheng; Xin Hua Duan; Le Liu

doi:10.1021/acs.orglett.4c03033

Photoredox Catalyzed Conia-Ene-Type Cyclization/Smiles Rearrangement Cascade Reactions to Access Substituted Methylenecarbocycles

Keyuan Zhang
, Qi Jiang
, Chonglong He
, Mingyou Hu
, Yangyang Cheng
, Xin Hua Duan
, Le Liu

School of Chemistry

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

10 Scopus citations

Abstract

We report a novel visible-light-driven photoredox-catalyzed cascade reaction involving Conia-ene-type cyclization and Smiles rearrangement initiated from alkyne-tethered α-sulfonyl esters. This methodology not only facilitates the rapid synthesis of a broad spectrum of highly substituted methylenecarbocycles but also introduces a new mechanistic pathway with aryl group migration, surpassing the conventional 1,5-hydrogen shift typically observed in Conia-ene reactions.

Original language	English
Pages (from-to)	7971-7975
Number of pages	5
Journal	Organic Letters
Volume	26
Issue number	37
DOIs	https://doi.org/10.1021/acs.orglett.4c03033
State	Published - 20 Sep 2024

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10.1021/acs.orglett.4c03033

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title = "Photoredox Catalyzed Conia-Ene-Type Cyclization/Smiles Rearrangement Cascade Reactions to Access Substituted Methylenecarbocycles",

abstract = "We report a novel visible-light-driven photoredox-catalyzed cascade reaction involving Conia-ene-type cyclization and Smiles rearrangement initiated from alkyne-tethered α-sulfonyl esters. This methodology not only facilitates the rapid synthesis of a broad spectrum of highly substituted methylenecarbocycles but also introduces a new mechanistic pathway with aryl group migration, surpassing the conventional 1,5-hydrogen shift typically observed in Conia-ene reactions.",

author = "Keyuan Zhang and Qi Jiang and Chonglong He and Mingyou Hu and Yangyang Cheng and Duan, \{Xin Hua\} and Le Liu",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

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doi = "10.1021/acs.orglett.4c03033",

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T1 - Photoredox Catalyzed Conia-Ene-Type Cyclization/Smiles Rearrangement Cascade Reactions to Access Substituted Methylenecarbocycles

AU - Zhang, Keyuan

AU - Jiang, Qi

AU - He, Chonglong

AU - Hu, Mingyou

AU - Cheng, Yangyang

AU - Duan, Xin Hua

AU - Liu, Le

PY - 2024/9/20

Y1 - 2024/9/20

N2 - We report a novel visible-light-driven photoredox-catalyzed cascade reaction involving Conia-ene-type cyclization and Smiles rearrangement initiated from alkyne-tethered α-sulfonyl esters. This methodology not only facilitates the rapid synthesis of a broad spectrum of highly substituted methylenecarbocycles but also introduces a new mechanistic pathway with aryl group migration, surpassing the conventional 1,5-hydrogen shift typically observed in Conia-ene reactions.

AB - We report a novel visible-light-driven photoredox-catalyzed cascade reaction involving Conia-ene-type cyclization and Smiles rearrangement initiated from alkyne-tethered α-sulfonyl esters. This methodology not only facilitates the rapid synthesis of a broad spectrum of highly substituted methylenecarbocycles but also introduces a new mechanistic pathway with aryl group migration, surpassing the conventional 1,5-hydrogen shift typically observed in Conia-ene reactions.

UR - https://www.scopus.com/pages/publications/85203816712

U2 - 10.1021/acs.orglett.4c03033

DO - 10.1021/acs.orglett.4c03033

M3 - 文章

C2 - 39259671

AN - SCOPUS:85203816712

SN - 1523-7060

VL - 26

SP - 7971

EP - 7975

JO - Organic Letters

JF - Organic Letters

IS - 37

ER -

Photoredox Catalyzed Conia-Ene-Type Cyclization/Smiles Rearrangement Cascade Reactions to Access Substituted Methylenecarbocycles

Abstract

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