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. 2022 Apr 25;61(18):e202117233.
doi: 10.1002/anie.202117233. Epub 2022 Mar 9.

Palladium(II)-Catalyzed Selective Arylation of Tertiary C-H Bonds of Cyclobutylmethyl Ketones Using Transient Directing Groups

Jin-Tang Cheng  1   2 , Li-Jun Xiao  1 , Shao-Qun Qian  1 , Zhe Zhuang  1 , An Liu  2 , Jin-Quan Yu  1
Affiliations

Palladium(II)-Catalyzed Selective Arylation of Tertiary C-H Bonds of Cyclobutylmethyl Ketones Using Transient Directing Groups

Jin-Tang Cheng et al. Angew Chem Int Ed Engl. .

Abstract

We report the first example of selective PdII -catalyzed tertiary C-H activation of cyclobutylmethyl ketones using a transient directing group. An electron-deficient 2-pyridone ligand was identified as the optimal external ligand to enable tertiary C-H activation. A variety of cyclobutylmethyl ketones bearing quaternary carbon centers was readily accessed without preinstalling internal directing groups in up to 81 % yield and >95 : 5 regioisomeric ratios of tertiary C-H arylation to β-methylene (β-methyl) or γ-C-H arylation.

Keywords: Arylation; C−H Activation; Palladium; Synthetic Methods; Transient Directing Group.

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Conflict of interest statement

Conflict of interest

The authors declare no conflict of interest.

Figures

Scheme 1.
Scheme 1.
Pd-catalyzed tertiary C‒H bond activation
See this image and copyright information in PMC

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