In recent years, there has been an ever-increasing interest in the field of metal-catalyzed C-H functionalizations and their application in the development of catalytic carbon-heteroatom bond formations for the synthesis of a wide variety of heterocycles. We have developed Cu and Fe-catalyzed allylic C-H amination methods to convert simple olefins, 1,3-dienes and a,b-unsaturated carbonyls to the corresponding N-aryl allylamines, dienyl allylamines, aza Baylis-Hillman adducts, etc. We have utilized N-aryl hydroxylamines and N-Boc hydroxylamine as aminating agents.<br/>Application of the developed methods to make biologically relevant heterocycles has also been explored. A direct method has been developed to make N-aryl-4-allyl oxazolidines via C-H amination and methylene group transfer. Another sequential catalytic approach is developed for the synthesis of N-heterocycles such as 2,3-disubstituted quinolines, 1,5-naphthyridines and 2-acylindolines (Fig. 1) via Fe-catalyzed allylic C-H amination followed by Heck-coupling. Method development, reaction pathways and synthetic applications of the developed reactions will be discussed.

Synthesis of organo nitrogen compounds and heterocycles via catalytic allylic C-H amination

249th National Meeting (2015)

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