Radical‐Induced, Palladium‐Catalyzed C‐H activation: A New Approach to Functionalize 4H‐Benzo[d][1,3]oxazin‐4‐one Derivatives with Toluenes, Aldehydes and Benzyl Alcohols

Prashant Kumar; Mohit Gupta; Vijay Bahadur; Virinder S. Parmar; Brajendra Kumar Singh

Index: 10.1002/ejoc.201800263

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Abstract

In the present work, toluenes, aldehydes and benzyl alcohols have been exploited in the radical‐induced direct functionalization of heterocyclic molecules, in particular 4H‐benzo[d][1,3]oxazin‐4‐one derivatives via the palladium‐catalyzed C‐H activation strategy. Greater stability, low toxicity and the easy access to toluenes, aldehydes and benzyl alcohols have made them suitable candidates for this transformation. The reaction in general proceeded smoothly and afforded the desired products in moderate to good yields with high functional group compatibility. Mechanistic investigations have illustrated the radical pathway and have highlighted the importance of both catalyst and oxidant.