Tunable Di- and Mono-γ-C−H Arylation of Phenylacetamides by Palladium-Catalyzed Domino Reactions

The Pd‐catalyzed C−H arylation of phenylacetamides in the γ position was realized for the first time by means of a domino process consisting of in situ directing group installation and C−H arylation. Unprecedented tunable selectivity between di‐ and monoactivation of the two identical γ‐C−H bonds wa...

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Bibliographic Details
Published in:ChemCatChem 2016-04, Vol.8 (8), p.1470-1473
Main Authors: Liu, Yunyun, Huang, Bin, Cao, Xiaoji, Wan, Jie-Ping
Format: Article
Language:English
Subjects:
C-H activation
domino reactions
molecular diversity
step economy
tunable selectivity
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Summary:The Pd‐catalyzed C−H arylation of phenylacetamides in the γ position was realized for the first time by means of a domino process consisting of in situ directing group installation and C−H arylation. Unprecedented tunable selectivity between di‐ and monoactivation of the two identical γ‐C−H bonds was achieved by modifying the reaction conditions; this is a distinct feature of this one‐pot procedure for the C−H‐activation‐based synthesis of diverse amides. One way or another: The palladium‐catalyzed C−H arylation of phenylacetamides in the γ position is realized by means of a domino process consisting of in situ directing group installation and C−H arylation. By modifying the reaction conditions, unprecedented selectivity between di‐ and monoarylation of the two identical γ‐C−H bonds is achieved. AQ=8‐aminoquinolinyl.
ISSN:1867-3880
1867-3899
DOI:10.1002/cctc.201600039