Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 18, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202117233
Keywords
Arylation; C-H Activation; Palladium; Synthetic Methods; Transient Directing Group
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Funding
- NIH (NIGMS) [R01GM084019]
- China Scholarship Council (CSC)
- China Academy of Chinese Medical Sciences [CI2021A04409]
- fundamental research funds for the central public welfare research institutes [ZZ13YQ-061]
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In this study, we report the first example of selective Pd(II)-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 achieve tertiary C-H activation. Various cyclobutylmethyl ketones with quaternary carbon centers were obtained in high yields without the need for preinstalling internal directing groups, and showed high regioselectivity for tertiary C-H arylation.
We report the first example of selective Pd-II-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 beta-methylene (beta-methyl) or gamma-C-H arylation.
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