Journal of Organic Chemistry

, volume 86 , issue 21 , pages 15717-15725

Perfluoroalkyl-Promoted Synthesis of Perfluoroalkylated Pyrrolidine-Fused Coumarins with Methyl β-Perfluoroalkylpropionates

Nan Ren ¹

Lingfeng Zhang ¹

Yijie Hu ¹

Xiaoli Wang ¹

Zhen Deng ¹

Jie Chen ¹

Hongmei Deng ²

Hui Zhang ²

Xiao‐Jun Tang ¹

Weiguo Cao ^{1, 3}

Hide authors affiliations Show authors affiliations: 3 affiliations

Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, China |

Laboratory for Microstructures and Instrumental Analysis and Research Center, Shanghai University, Shanghai, 200444, China |

Key laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China |

Publication type: Journal Article

Publication date: 2021-10-13

American Chemical Society (ACS)

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR: 0.737

CiteScore: 6.1

Impact factor: 3.6

ISSN: 00223263, 15206904

DOI: 10.1021/acs.joc.1c01538

Copy DOI

PubMed ID: 34644085

Organic Chemistry

Abstract

Employing the methyl β-perfluoroalkylpropionate as the Michael acceptor, an efficient approach for the synthesis of perfluoroalkylated pyrrolidine-fused coumarins has been achieved. A tandem reaction involving [3 + 2] cycloaddition and intramolecular transesterification was proposed for the mechanism. The enhanced electrophilicity resulting from the strong electron-withdrawing ability of the perfluoroalkyl group was crucial for this tandem reaction.

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GOST |

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GOST Copy

Ren N. et al. Perfluoroalkyl-Promoted Synthesis of Perfluoroalkylated Pyrrolidine-Fused Coumarins with Methyl β-Perfluoroalkylpropionates // Journal of Organic Chemistry. 2021. Vol. 86. No. 21. pp. 15717-15725.

GOST all authors (up to 50) Copy

Ren N., Zhang L., Hu Y., Wang X., Deng Z., Chen J., Deng H., Zhang H., Tang X., Cao W. Perfluoroalkyl-Promoted Synthesis of Perfluoroalkylated Pyrrolidine-Fused Coumarins with Methyl β-Perfluoroalkylpropionates // Journal of Organic Chemistry. 2021. Vol. 86. No. 21. pp. 15717-15725.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.joc.1c01538

UR - https://doi.org/10.1021/acs.joc.1c01538

TI - Perfluoroalkyl-Promoted Synthesis of Perfluoroalkylated Pyrrolidine-Fused Coumarins with Methyl β-Perfluoroalkylpropionates

T2 - Journal of Organic Chemistry

AU - Ren, Nan

AU - Zhang, Lingfeng

AU - Hu, Yijie

AU - Wang, Xiaoli

AU - Deng, Zhen

AU - Chen, Jie

AU - Deng, Hongmei

AU - Zhang, Hui

AU - Tang, Xiao‐Jun

AU - Cao, Weiguo

PY - 2021

DA - 2021/10/13

PB - American Chemical Society (ACS)

SP - 15717-15725

IS - 21

VL - 86

PMID - 34644085

SN - 0022-3263

SN - 1520-6904

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2021_Ren,

author = {Nan Ren and Lingfeng Zhang and Yijie Hu and Xiaoli Wang and Zhen Deng and Jie Chen and Hongmei Deng and Hui Zhang and Xiao‐Jun Tang and Weiguo Cao},

title = {Perfluoroalkyl-Promoted Synthesis of Perfluoroalkylated Pyrrolidine-Fused Coumarins with Methyl β-Perfluoroalkylpropionates},

journal = {Journal of Organic Chemistry},

year = {2021},

volume = {86},

publisher = {American Chemical Society (ACS)},

month = {oct},

url = {https://doi.org/10.1021/acs.joc.1c01538},

number = {21},

pages = {15717--15725},

doi = {10.1021/acs.joc.1c01538}

}

MLA

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MLA Copy

Ren, Nan, et al. “Perfluoroalkyl-Promoted Synthesis of Perfluoroalkylated Pyrrolidine-Fused Coumarins with Methyl β-Perfluoroalkylpropionates.” Journal of Organic Chemistry, vol. 86, no. 21, Oct. 2021, pp. 15717-15725. https://doi.org/10.1021/acs.joc.1c01538.

Publisher

American Chemical Society (ACS)

Journal

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR

0.737

CiteScore

6.1

Impact factor

3.6

ISSN

00223263 (Print)

15206904 (Electronic)