Due to the ubiquity of nitrogen moiety in various natural and pharmaceutical products, the construction of C-N bond in a step economical manner via transition metal-catalyzed C H amination reaction has attracted much attention in organic synthesis. The allylic C H bond of terminal alkenes can be activated very effectively in the presence of a palladium catalyst (via π-allyl mechanism)1 or low valent Iridium complexes2 (by allylic substitution reactions) in the presence of labile leaving group at the allylic position are well known. Recently, Rh(III) and Ir(III) catalyzed intermolecular C H amination, etherification and C C bond formation of various alkenes with N, O and C nucleophiles has been reported. Among the widely utilized aminating reagents, iminoiodinane is a viable nitrene precursor and efficient amidation source to carry out C-H insertion or aziridination reactions in inter- as well as intramolecular manner. In this conference, we are going to present the idea of amide functionalization of unactivated olefins by avoiding the usage of metal oxidants. The iminoiodinane precursors can be derived by in situ oxidation of sulfonamide with the environment benign and easily available hypervalent iodine oxidants. This also overcomes the pitfalls of the synthesis and characterization of iminoiodinanes. This protocol is compatible with differently functionalized unactivated terminal alkenes and internal alkenes. A possible reaction mechanism involving π-allyl and metal-nitrene intermediate has been proposed. The nosyl group deprotection is carried out to obtain corresponding allylic amines in internal and terminal alkene cases.

Rh(III) catalyzed allylic C-H amidation of unactivated alkenes with in situ generated iminoiodinanes by using organic oxidant

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27th CRSI National Symposium in Chemistry

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