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N‐Directed Pd‐Catalyzed Direct ortho ‐Acetoxylation and ortho ‐ tert ‐Butoxylation of 2‐Phenyl‐4 H ‐benzo[ d ][1,3]oxazin‐4‐ones via C‐H Activation
Author(s) -
Gupta Mohit,
Kumar Sandeep,
Kumar Prashant,
Kumar Singh Amit,
Bahadur Vijay,
K. Singh Brajendra
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201902755
Subject(s) - regioselectivity , indoline , catalysis , chemistry , substrate (aquarium) , functional group , medicinal chemistry , stereochemistry , palladium , group (periodic table) , combinatorial chemistry , organic chemistry , polymer , geology , oceanography
A highly efficient, palladium‐catalyzed protocol for the regioselective ortho ‐acyloxylation of 4 H ‐Benzo[ d ][1,3]oxazin‐4‐ones and various other heterocycles which includes indoline, 3,4‐dihydro‐2 H ‐benzo[ b ][1,4]oxazine, and 1‐methyl‐3‐phenylquinoxalin‐2(1 H )‐one has been developed using C−H activation strategy. The protocol exploits the directing group property of nitrogen present in the heterocyclic framework to introduce the acyloxyl group onto heterocyclic compounds with excellent regioselectivity. The developed method offers a wide substrate and excellent functional group tolerance.