Palladium‐Catalyzed Olefination of 4H‐Benzo[d][1,3]oxazin‐4‐one Derivatives with Activated Alkenes via Preferential Cyclic Imine‐N‐Directed Aryl C‐H Activation

• Published in: European journal of organic chemistry Vol. 2019; no. 33; pp. 5777 - 5786
• Main Authors: Panja, Subir, Maity, Srabani, Majhi, Biju, Ranu, Brindaban C.
• Format: Journal Article
• Language: English
• Published: 08-09-2019
• Subjects: C‐H activation; Heterocycles; Olefination; Palladium; Regioselectivity
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201900935

A palladium‐catalyzed chelation‐assisted selective ortho C‐H bond olefination of biologically active 4H‐benzo[d][1,3] oxazin‐4‐one derivatives with activated olefins has been achieved. The products are obtained in good yields with high regio‐ and stereoselectivities. This new protocol has been demonstrated to provide a variety of olefinated‐4H‐benzo[d][1,3]oxazin‐4‐one derivatives. The site selectivity of the reaction was explained by a DFT study.
An efficient procedure for the Pd‐catalyzed olefination of 4H‐benzo[d][1,3]oxazin‐4‐ones with activated alkenes has been achieved via C‐H activation. The site selectivity of the reaction was explained by a DFT study.