Synthesis of Dihydroisoquinolone-Fused Cyclobutanes via Tandem Palladium-Mediated Olefin Migration and Photosensitized [2 + 2] Cycloaddition

A tandem palladium-mediated olefin migration and visible light-promoted [2 + 2] cycloaddition reaction was disclosed. It provides a facile method to synthesize the cyclobutane-fused dihydroisoquinolone-based polycycles bearing a methyl group. Further product derivatization enables the efficient construction of diverse cyclobutane derivatives. Mechanistic studies revealed that the palladium catalysts promoted the olefin migration and inhibited the direct [2 + 2] cyclization of substrates.

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Publication Details

Journal
Organic Letters
Published
2025-10-28
DOI
https://doi.org/10.1021/acs.orglett.5c03602
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Synthesis of Dihydroisoquinolone-Fused Cyclobutanes via Tandem Palladium-Mediated Olefin Migration and Photosensitized [2 + 2] Cycloaddition

Siping Wei, Qiang Fu, Yimou Gong, Zhijie Zhang et al.
Organic Letters
Catalytic C–H Functionalization Methods
article

Synthesis of Dihydroisoquinolone-Fused Cyclobutanes via Tandem Palladium-Mediated Olefin Migration and Photosensitized [2 + 2] Cycloaddition

Siping Wei, Qiang Fu, Yimou Gong, Zhijie Zhang, Xiong Cheng, Zhen Xiang, Jing Peng, Chuan Feng
article en

Abstract

A tandem palladium-mediated olefin migration and visible light-promoted [2 + 2] cycloaddition reaction was disclosed. It provides a facile method to synthesize the cyclobutane-fused dihydroisoquinolone-based polycycles bearing a methyl group. Further product derivatization enables the efficient construction of diverse cyclobutane derivatives. Mechanistic studies revealed that the palladium catalysts promoted the olefin migration and inhibited the direct [2 + 2] cyclization of substrates.

Organic LettersVol. 27(44)
Southwest Medical University (CN), First Affiliated Hospital of Sichuan Medical University (CN), Green Chemistry (PL)
Openalex Percentile: Top 76%
Catalytic C–H Functionalization Methods
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