Copper‐Catalyzed C‐4 Carboxylation of 1‐Naphthylamide Derivatives with CBr4/MeOH

A simple and practical copper catalyzed C‐4 carboxylation reaction of 1‐naphthylamide derivatives using carbon tetra bromide and methanol is reported here. Picolinamide and its derivatives are used as a bidentate directing group for the distal C4‐H functionalization. Various substituted naphthylamid...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2019-09, Vol.361 (17), p.3950-3957
Main Authors: Sahoo, Tapan, Sen, Chiranjit, Singh, Harshvardhan, Suresh, E., Ghosh, Subhash Chandra
Format: Article
Language:English
Subjects:
1-naphthaylamide
Carboxylation
Copper
Copper-catalyzed
Derivatives
Electron transfer
Electrons
regioselective
SET
Single electrons
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Summary:A simple and practical copper catalyzed C‐4 carboxylation reaction of 1‐naphthylamide derivatives using carbon tetra bromide and methanol is reported here. Picolinamide and its derivatives are used as a bidentate directing group for the distal C4‐H functionalization. Various substituted naphthylamide derivatives, and anilides are employed for the carboxylation and proceeds in good yields under mild condition. From the outcome of experimental results, it is proposed that C4‐H carboxylation reaction of 1‐naphthylamides might proceed through a single electron transfer (SET) pathway.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201900482