B(C6F5)3-Catalyzed [2+3]-Cyclative o,m-diC-H Functionalization of Phenols

Jingyan Luo; Zhou Luo; Biqi Zhang; Qiuyu Zhao; Lu Liu; Yuanyuan Liu

doi:10.1002/chem.202301595

B(C₆F₅)₃-Catalyzed [2+3]-Cyclative o,m-diC-H Functionalization of Phenols

Jingyan Luo
, Zhou Luo
, Biqi Zhang
, Qiuyu Zhao
, Lu Liu
, Yuanyuan Liu^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

Abstract

Metal-free catalytic C−H functionalization is highly desired for the construction of C−C bonds. We herein report a highly chemoselective consecutive C−H [2+3]-cyclative functionalization for the simultaneous formation of two C−C bonds with construction of polycyclic phenols catalyzed by commercially available and low-cost B(C₆F₅)₃. This catalytic system tolerates a wide range of substrate scope, providing a series of 2,6,7,8-tetrahydroacenaphthylen-3-ol-type polycyclic compounds efficiently. Several derivatizations of the catalytic products have also been conducted to show the potential application of this method in synthesis of polycyclic compounds.

Original language	English
Article number	e202301595
Journal	Chemistry - A European Journal
Volume	29
Issue number	71
DOIs	https://doi.org/10.1002/chem.202301595
State	Published - 19 Dec 2023

Keywords

B(CF)
C−H functionalization
[2+3] cyclization
phenols
polycyclic compounds

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10.1002/chem.202301595

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@article{060b00ab204f403cbb84d73b58b53a25,

title = "B(C6F5)3-Catalyzed [2+3]-Cyclative o,m-diC-H Functionalization of Phenols",

abstract = "Metal-free catalytic C−H functionalization is highly desired for the construction of C−C bonds. We herein report a highly chemoselective consecutive C−H [2+3]-cyclative functionalization for the simultaneous formation of two C−C bonds with construction of polycyclic phenols catalyzed by commercially available and low-cost B(C6F5)3. This catalytic system tolerates a wide range of substrate scope, providing a series of 2,6,7,8-tetrahydroacenaphthylen-3-ol-type polycyclic compounds efficiently. Several derivatizations of the catalytic products have also been conducted to show the potential application of this method in synthesis of polycyclic compounds.",

keywords = "B(CF), C−H functionalization, [2+3] cyclization, phenols, polycyclic compounds",

author = "Jingyan Luo and Zhou Luo and Biqi Zhang and Qiuyu Zhao and Lu Liu and Yuanyuan Liu",

note = "Publisher Copyright: {\textcopyright} 2023 Wiley-VCH GmbH.",

year = "2023",

month = dec,

day = "19",

doi = "10.1002/chem.202301595",

language = "英语",

volume = "29",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley and Sons Inc",

number = "71",

}

TY - JOUR

T1 - B(C6F5)3-Catalyzed [2+3]-Cyclative o,m-diC-H Functionalization of Phenols

AU - Luo, Jingyan

AU - Luo, Zhou

AU - Zhang, Biqi

AU - Zhao, Qiuyu

AU - Liu, Lu

AU - Liu, Yuanyuan

PY - 2023/12/19

Y1 - 2023/12/19

N2 - Metal-free catalytic C−H functionalization is highly desired for the construction of C−C bonds. We herein report a highly chemoselective consecutive C−H [2+3]-cyclative functionalization for the simultaneous formation of two C−C bonds with construction of polycyclic phenols catalyzed by commercially available and low-cost B(C6F5)3. This catalytic system tolerates a wide range of substrate scope, providing a series of 2,6,7,8-tetrahydroacenaphthylen-3-ol-type polycyclic compounds efficiently. Several derivatizations of the catalytic products have also been conducted to show the potential application of this method in synthesis of polycyclic compounds.

AB - Metal-free catalytic C−H functionalization is highly desired for the construction of C−C bonds. We herein report a highly chemoselective consecutive C−H [2+3]-cyclative functionalization for the simultaneous formation of two C−C bonds with construction of polycyclic phenols catalyzed by commercially available and low-cost B(C6F5)3. This catalytic system tolerates a wide range of substrate scope, providing a series of 2,6,7,8-tetrahydroacenaphthylen-3-ol-type polycyclic compounds efficiently. Several derivatizations of the catalytic products have also been conducted to show the potential application of this method in synthesis of polycyclic compounds.

KW - B(CF)

KW - C−H functionalization

KW - [2+3] cyclization

KW - phenols

KW - polycyclic compounds

UR - https://www.scopus.com/pages/publications/85175556188

U2 - 10.1002/chem.202301595

DO - 10.1002/chem.202301595

M3 - 文章

C2 - 37759356

AN - SCOPUS:85175556188

SN - 0947-6539

VL - 29

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 71

M1 - e202301595

ER -

B(C₆F₅)₃-Catalyzed [2+3]-Cyclative o,m-diC-H Functionalization of Phenols

Abstract

Keywords

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