Heteroarylation of unactivated C-H bonds suitable for late-stage functionalization.

The late-stage introduction of diverse heterocycles onto complex small molecules enables efficient access to new medicinally relevant compounds. An attractive approach to such a transformation would utilize the ubiquitous aliphatic C-H bonds of a complex substrate. Herein, we report a system that enables direct C-H heteroarylation using a stable, commercially available -alkenylhydroxamate with heterocyclic sulfone partners.

Diversification of aliphatic C-H bonds in small molecules and polyolefins through radical chain transfer.

The ability to selectively introduce diverse functionality onto hydrocarbons is of substantial value in the synthesis of both small molecules and polymers. Herein, we report an approach to aliphatic carbon-hydrogen bond diversification using radical chain transfer featuring an easily prepared -alkenylhydroxamate reagent, which upon mild heating facilitates a range of challenging or previously undeveloped aliphatic carbon-hydrogen bond functionalizations of small molecules and polyolefins. This broad reaction platform enabled the functionalization of postconsumer polyolefins in infrastructure used to process plastic waste.