Redox-neutral remote amidation of alkenyl alcohols via long-range isomerization/transformation

Abstract

The long-range isomerization/transformation of alkenyl alcohols represents one of the most important classes of chemical transformations, but related remote amidations with amines are scarce. Herein, we report a redox-neutral Ru-catalyzed cross-coupling reaction of long-range alkenyl alcohols with amines to produce the corresponding amides by a “chain-walking” strategy which is a powerful approach to realize remote site-selective functionalization. The catalyzed movement of an alkene double bond in alkenyl alcohols over 9 positions along an alkyl chain has been realized. A range of easily accessible alkenyl alcohols can be converted in a rapidly assembled fashion to valuable amides with good yields and wide functional group tolerance.