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Tandem Oxidation-Dehydrogenation of (Hetero)Arylated Primary Alcohols via Perruthenate Catalysis

Tandem Oxidation-Dehydrogenation of (Hetero)Arylated Primary Alcohols via Perruthenate Catalysis Tandem oxidative-dehydrogenation of primary alcohols to give ,-unsaturated aldehydes in one pot are rare transformations in organic synthesis, with only two methods currently available. Reported herein is a novel method using the bench-stable salt methyltriphenylphosphonium perruthenate (MTP3), and a new co-oxidant NEMOPF6 (NEMON-ethyl-N-hydroxymorpholinium) which provides unsaturated aldehydes in low to moderate yields. The Ley-Griffith oxidation of (hetero)arylated primary alcohols with N-oxide co-oxidants NMO (NMON-methylmorpholine N-oxide)/NEMO, is expanded by addition of the N-oxide salt NEMOPF6 to convert the intermediate saturated aldehyde into its unsaturated counterpart. The discovery, method development, reaction scope, and associated challenges of this method are highlighted. The conceptual value of late-stage dehydrogenation in natural product synthesis is demonstrated via the synthesis of a polyene scaffold related to auxarconjugatin B. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Australian Journal of Chemistry CSIRO Publishing

Tandem Oxidation-Dehydrogenation of (Hetero)Arylated Primary Alcohols via Perruthenate Catalysis

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References (5)

Publisher
CSIRO Publishing
Copyright
Copyright © The Author(s). Published by CSIRO Publishing
ISSN
0004-9425
eISSN
1445-0038
DOI
10.1071/CH21137
Publisher site
See Article on Publisher Site

Abstract

Tandem oxidative-dehydrogenation of primary alcohols to give ,-unsaturated aldehydes in one pot are rare transformations in organic synthesis, with only two methods currently available. Reported herein is a novel method using the bench-stable salt methyltriphenylphosphonium perruthenate (MTP3), and a new co-oxidant NEMOPF6 (NEMON-ethyl-N-hydroxymorpholinium) which provides unsaturated aldehydes in low to moderate yields. The Ley-Griffith oxidation of (hetero)arylated primary alcohols with N-oxide co-oxidants NMO (NMON-methylmorpholine N-oxide)/NEMO, is expanded by addition of the N-oxide salt NEMOPF6 to convert the intermediate saturated aldehyde into its unsaturated counterpart. The discovery, method development, reaction scope, and associated challenges of this method are highlighted. The conceptual value of late-stage dehydrogenation in natural product synthesis is demonstrated via the synthesis of a polyene scaffold related to auxarconjugatin B.

Journal

Australian Journal of Chemistry – CSIRO Publishing

Published: Aug 30, 2021

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