Reactions that selectively functionalize aliphatic C−H bonds possess the powerful ability to streamline complex molecule synthesis. Few completely intermolecular C-H functionalizations exist, however, that are synthetically useful. We have recently developed an approach to unactivated, aliphatic C−H halogenation using easily prepared N-haloamide reagents. These halogenations proceed in good chemical yields, with substrate as the limiting reagent in all cases. The use of substrate as the limiting reagent is particularly important in applying our method to late-stage functionalizations. The site selectivities of these radical-mediated C− H functionalizations are comparable or superior to the most selective intermolecular C−H functionalizations known. With the broad utility of alkyl halides as synthetic intermediates, we expect our approach will find general use in chemical synthesis.<br/>

Site-selective aliphatic C-H halogenation using N-haloamides

249th National Meeting (2015)

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