Selective oxidation of alcohol-d₁ to aldehyde-d₁ using MnO₂

Abstract

A facile method for deutrium incorporation into aldehydes by mild reduction of NaBD4 of aldehydes and MnO2 oxidation (98% D) is disclosed.

Synthesis and properties of covalently linked phenyl bridged 3-pyrrolyl BODIPY–BODIPY dyads

“…The crude compound was purified by silica gel column chromatography, yielding 3-pyrrolyl BODIPY 7 , containing a p -hydroxymethylphenyl group at the meso -position as a red fluorescent solid in 20% yield. Compound 7 was further subjected to oxidation 27 with MnO 2 , resulting in the formation of meso -4-formylphenyl-3-pyrrolyl BODIPY 8 in 90% yield. Compound 8 was then reacted with excess pyrrole under acid catalyzed conditions to obtain meso -dipyrromethanyl 3-pyrrolyl BODIPY 9 .…”

An In‐Situ‐Formed Copper‐Based Perfluorinated Catalytic System for the Aerobic Oxidation of Alcohols

“…Additional references cited within the Supporting Information. [31][32][33][34][35][36][37][38][39][40][41]…”

Modelling kinetic isotope effects for Swern oxidation using DFT-based transition state theory

“…Recently, several reports have documented the oxidation of monodeuterated alcohols to deuterated-enriched aldehydes at synthetically useful levels (85-98 atom% D) by exploitation of a kinetic isotope effect (KIE). [1][2][3][4] These methods provide a convenient alternative to pre-existing syntheses of C 1 -deuterated alcohols 5,6 since they allow the use of the relatively inexpensive NaBD 4 to install one deuterium atom by reaction with an aldehyde, followed by reoxidation using standard oxidation reagents. The oxidation reagents reported to be successful so far for this latter process are pyridinium chlorochromate-silica, 1 manganese dioxide 2 and pyridinium chlorochromate.…”