Chemo-Divergent Friedel–Crafts Alkylation and Friedel–Crafts Acylation of Arenes with α-Diazo Ketones Tuned by Reaction Conditions

Xinrong Zhi; Xinyu Huang; Xin Ji; Lu Liu

doi:10.1002/cmtd.202500108

Chemo-Divergent Friedel–Crafts Alkylation and Friedel–Crafts Acylation of Arenes with α-Diazo Ketones Tuned by Reaction Conditions

Xinrong Zhi, Xinyu Huang, Xin Ji, Lu Liu^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

Abstract

A chemo-divergent Friedel–Crafts alkylation and Friedel–Crafts acylation of arenes with α-diazo ketones has been developed. In this reaction, Cu(OTf)₂ catalyzed the Friedel–Crafts alkylation via Cu-carbene intermediate, while hexafluoroisopropanol (HFIP) promoted the Friedel–Crafts acylation via the ketene intermediate. This protocol provides a controllable aromatic C(sp2).H bond functionalization of arenes by tuning the reaction conditions.

Original language	English
Journal	Chemistry-Methods
DOIs	https://doi.org/10.1002/cmtd.202500108
State	Accepted/In press - 2025

Keywords

C.H bond functionalization
diazo ketones
Friedel-Crafts alkylation
Friedel–Crafts acylation
ketene

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10.1002/cmtd.202500108

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title = "Chemo-Divergent Friedel–Crafts Alkylation and Friedel–Crafts Acylation of Arenes with α-Diazo Ketones Tuned by Reaction Conditions",

abstract = "A chemo-divergent Friedel–Crafts alkylation and Friedel–Crafts acylation of arenes with α-diazo ketones has been developed. In this reaction, Cu(OTf)2 catalyzed the Friedel–Crafts alkylation via Cu-carbene intermediate, while hexafluoroisopropanol (HFIP) promoted the Friedel–Crafts acylation via the ketene intermediate. This protocol provides a controllable aromatic C(sp2).H bond functionalization of arenes by tuning the reaction conditions.",

keywords = "C.H bond functionalization, diazo ketones, Friedel-Crafts alkylation, Friedel–Crafts acylation, ketene",

author = "Xinrong Zhi and Xinyu Huang and Xin Ji and Lu Liu",

note = "Publisher Copyright: {\textcopyright} 2025 The Author(s). Chemistry - Methods published by Chemistry Europe and Wiley-VCH GmbH.",

year = "2025",

doi = "10.1002/cmtd.202500108",

language = "英语",

journal = "Chemistry-Methods",

issn = "2628-9725",

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TY - JOUR

T1 - Chemo-Divergent Friedel–Crafts Alkylation and Friedel–Crafts Acylation of Arenes with α-Diazo Ketones Tuned by Reaction Conditions

AU - Zhi, Xinrong

AU - Huang, Xinyu

AU - Ji, Xin

AU - Liu, Lu

PY - 2025

Y1 - 2025

N2 - A chemo-divergent Friedel–Crafts alkylation and Friedel–Crafts acylation of arenes with α-diazo ketones has been developed. In this reaction, Cu(OTf)2 catalyzed the Friedel–Crafts alkylation via Cu-carbene intermediate, while hexafluoroisopropanol (HFIP) promoted the Friedel–Crafts acylation via the ketene intermediate. This protocol provides a controllable aromatic C(sp2).H bond functionalization of arenes by tuning the reaction conditions.

AB - A chemo-divergent Friedel–Crafts alkylation and Friedel–Crafts acylation of arenes with α-diazo ketones has been developed. In this reaction, Cu(OTf)2 catalyzed the Friedel–Crafts alkylation via Cu-carbene intermediate, while hexafluoroisopropanol (HFIP) promoted the Friedel–Crafts acylation via the ketene intermediate. This protocol provides a controllable aromatic C(sp2).H bond functionalization of arenes by tuning the reaction conditions.

KW - C.H bond functionalization

KW - diazo ketones

KW - Friedel-Crafts alkylation

KW - Friedel–Crafts acylation

KW - ketene

UR - https://www.scopus.com/pages/publications/105020706449

U2 - 10.1002/cmtd.202500108

DO - 10.1002/cmtd.202500108

M3 - 文章

AN - SCOPUS:105020706449

SN - 2628-9725

JO - Chemistry-Methods

JF - Chemistry-Methods

ER -

Chemo-Divergent Friedel–Crafts Alkylation and Friedel–Crafts Acylation of Arenes with α-Diazo Ketones Tuned by Reaction Conditions

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Keywords

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