Highly Chemo- and Site-Selective Aromatic C-H Bond Functionalization of Phenols with α-Aryl-α-diazoketones via Gold Catalysis

Juncai Ma; Mingjia Li; Zhi Yao Si; Xun Shen Liu; Lu Liu

doi:10.1055/a-2851-2548

Highly Chemo- and Site-Selective Aromatic C-H Bond Functionalization of Phenols with α-Aryl-α-diazoketones via Gold Catalysis

Juncai Ma
, Mingjia Li
, Zhi Yao Si
, Xun Shen Liu
, Lu Liu^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development
East China Normal University
Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan
Shihezi University

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

Abstract

Herein, we report the direct C(sp²)-H functionalization of unprotected phenols with α-aryl α-diazoketones using gold complexes derived from tris(2,4-di-tert-butylphenyl) phosphite. This protocol features readily available starting materials, exclusive C(sp²)-H functionalization, suppressed O-H insertion, and inhibited Wolff rearrangement, along with broad substrate scope, mild conditions, high conversion, and facile product derivatization. It provides a novel strategy for selective C(sp²)-H functionalization, expanding gold-catalyzed carbene chemistry utility.

Original language	English
Pages (from-to)	1227-1231
Number of pages	5
Journal	Synlett
Volume	37
Issue number	11
DOIs	https://doi.org/10.1055/a-2851-2548
State	Published - 1 Jul 2026

Keywords

C-H bond functionalization
alkylation
carbenes
diazoketones
gold catalysis

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10.1055/a-2851-2548

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title = "Highly Chemo- and Site-Selective Aromatic C-H Bond Functionalization of Phenols with α-Aryl-α-diazoketones via Gold Catalysis",

abstract = "Herein, we report the direct C(sp2)-H functionalization of unprotected phenols with α-aryl α-diazoketones using gold complexes derived from tris(2,4-di-tert-butylphenyl) phosphite. This protocol features readily available starting materials, exclusive C(sp2)-H functionalization, suppressed O-H insertion, and inhibited Wolff rearrangement, along with broad substrate scope, mild conditions, high conversion, and facile product derivatization. It provides a novel strategy for selective C(sp2)-H functionalization, expanding gold-catalyzed carbene chemistry utility.",

keywords = "C-H bond functionalization, alkylation, carbenes, diazoketones, gold catalysis",

author = "Juncai Ma and Mingjia Li and Si, \{Zhi Yao\} and Liu, \{Xun Shen\} and Lu Liu",

year = "2026",

month = jul,

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doi = "10.1055/a-2851-2548",

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volume = "37",

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journal = "Synlett",

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TY - JOUR

T1 - Highly Chemo- and Site-Selective Aromatic C-H Bond Functionalization of Phenols with α-Aryl-α-diazoketones via Gold Catalysis

AU - Ma, Juncai

AU - Li, Mingjia

AU - Si, Zhi Yao

AU - Liu, Xun Shen

AU - Liu, Lu

PY - 2026/7/1

Y1 - 2026/7/1

N2 - Herein, we report the direct C(sp2)-H functionalization of unprotected phenols with α-aryl α-diazoketones using gold complexes derived from tris(2,4-di-tert-butylphenyl) phosphite. This protocol features readily available starting materials, exclusive C(sp2)-H functionalization, suppressed O-H insertion, and inhibited Wolff rearrangement, along with broad substrate scope, mild conditions, high conversion, and facile product derivatization. It provides a novel strategy for selective C(sp2)-H functionalization, expanding gold-catalyzed carbene chemistry utility.

AB - Herein, we report the direct C(sp2)-H functionalization of unprotected phenols with α-aryl α-diazoketones using gold complexes derived from tris(2,4-di-tert-butylphenyl) phosphite. This protocol features readily available starting materials, exclusive C(sp2)-H functionalization, suppressed O-H insertion, and inhibited Wolff rearrangement, along with broad substrate scope, mild conditions, high conversion, and facile product derivatization. It provides a novel strategy for selective C(sp2)-H functionalization, expanding gold-catalyzed carbene chemistry utility.

KW - C-H bond functionalization

KW - alkylation

KW - carbenes

KW - diazoketones

KW - gold catalysis

UR - https://www.scopus.com/pages/publications/105043374666

U2 - 10.1055/a-2851-2548

DO - 10.1055/a-2851-2548

M3 - 文章

AN - SCOPUS:105043374666

SN - 0936-5214

VL - 37

SP - 1227

EP - 1231

JO - Synlett

JF - Synlett

IS - 11

ER -

Highly Chemo- and Site-Selective Aromatic C-H Bond Functionalization of Phenols with α-Aryl-α-diazoketones via Gold Catalysis

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