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

Organic Chemistry Frontiers Pub Date: 2022-09-14 DOI: 10.1039/D2QO01143C

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.

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