Rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes: Effective conversion of amines and anilines into amides

Zhao Wu, Kami L. Hull

Research output: Contribution to journalArticlepeer-review

Abstract

The rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes is reported. In situ generated [(BINAP)Rh]BF4 catalyzes the one-pot isomerization/oxidative amidation of allylic alcohols or direct amidation of aldehydes using acetone or styrene as the hydrogen acceptor. The conditions are general, affording good to excellent yields with a wide array of amine and aniline nucleophiles, and chemoselective, other alcohols do not participate in the oxidation reaction. Utilization of biphasic conditions is critical, as they promote an equilibrium between the imine/enamine byproducts and the hemiaminal, which can undergo oxidation to the amide.

Original languageEnglish (US)
Pages (from-to)969-975
Number of pages7
JournalChemical Science
Volume7
Issue number2
DOIs
StatePublished - 2016

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes: Effective conversion of amines and anilines into amides'. Together they form a unique fingerprint.

Cite this