Palladium-catalyzed oxamidation of alkenes: A new approach to benzoxazolidines

A novel palladium catalyzed protocol for the synthesis of benzoxazolidine by the reaction sulfamidophenol and terminal alkene was developed. This oxamidation process is simple and does not require any ligand, base or inert atmosphere for the overall transformation. From control experiments, it is ap...

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Bibliographic Details
Published in:Tetrahedron 2018-03, Vol.74 (13), p.1497-1504
Main Authors: Panda, Niranjan, Yadav, Sushree Arpitabala
Format: Article
Language:English
Subjects:
Alkene
Benzoxazolidine
Oxamidation
Protodepalladation
Sulfonamide
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Summary:A novel palladium catalyzed protocol for the synthesis of benzoxazolidine by the reaction sulfamidophenol and terminal alkene was developed. This oxamidation process is simple and does not require any ligand, base or inert atmosphere for the overall transformation. From control experiments, it is apparent that the cross-coupling reaction proceeds with initial formation of enesulfonamide which undergoes nucleopalladation by the intramolecular annulation and subsequent protodepalladation by TsOH to afford the benzoxazolidine. [Display omitted] •An alternate route to benzoxazolidine synthesis was reported.•A protocol for palladium-catalyzed oxamidation of alkene was presented.•Nucleopalladation and protodepalladation of the in-situ generated enesulfonamide is the key-step to access benzoxazolidine.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.02.012