@article {35356,
	title = {Direct, Catalytic α-Alkylation of N-Heterocycles by Hydroaminoalkylation: Substrate Effects for Regiodivergent Product Formation},
	journal = {Journal of the American Chemical Society.},
	volume = {143},
	year = {2021},
	chapter = {11243-11250},
	abstract = {<p>Saturated N-heterocycles are prevalent in pharmaceutical and agrochemical industries, yet remain challenging to catalytically alkylate. Most strategies for C\&ndash;H activation of these challenging substrates use protected amines or high loadings of precious metal catalysts. We report an early transition-metal system for the broad, robust, and direct alkylation of unprotected amine heterocycles with simple alkenes. Short reaction times are achieved using an in situ generated tantalum catalyst that avoids the use of bases, excess substrate, or additives. In most cases, this catalyst system is selective for the branched reaction product, including examples of products that are generated with excellent diastereoselectivity. Alkene electronic properties can be exploited for substrate-modified regioselectivity to access the alternative linear amine alkylation product with a group 5 catalyst. This method allows for the facile isolation of unprotected N-heterocyclic products, as useful substrates for further reactivity.</p>},
	author = {DiPucchio, R. C. and Lenzen, K. E. and Daneshmand, P. and Ezhova, M. B. and Schafer, L. L.}
}
