Allylic Amination via Decarboxylative C-N Bond Formation

Abstract

This manuscript details the development of a palladium-catalyzed allylic amination that proceeds via decarboxylation of ­allylic carbamates. Both saturated and aromatic heterocycles undergo decarboxylative rearrangement in good yields. The mechanism of allylation of heteroaromatic amines involves the formation of π-allyl palladium complexes followed by decarboxylation of the ­carbamate. Finally, the heteroaromatic anion equivalent is allylated to provide allylic amines.

Key words

palladium-catalyzed - decarboxylation - allylic amination

References

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12

Our attempts to utilize Ni(0) catalysts for decarboxylative allylation yielded mainly 1,5-dienes via allyl homodimerization.