A Versatile and Highly Selective Hypervalent Iodine (III)/2,2,6,6-Tetramethyl-1-piperidinyloxyl-Mediated Oxidation of Alcohols to Carbonyl Compounds

Abstract

Catalytic amounts of 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) are used in combination with [bis(acetoxy)iodo]benzene (BAIB) as a stoichiometric oxidant in the conversion of primary and secondary alcohols to carbonyl compounds. This procedure works efficiently at room temperature in almost all common solvents and neat in some cases. This process exhibits a very high degree of selectivity for the oxidation of primary alcohols to aldehydes, without any noticeable overoxidation to carboxyl compounds, and a high chemoselectivity in the presence of either secondary alcohols or of other oxidizable moieties. This procedure allows an easy, convenient, high-yielding method for the oxidation of alcohols starting from commercially available compounds.

Recent Applications of the Suzuki-Miyaura Cross-coupling to Complex Polycyclic Ether Synthesis

“…In the course of our studies, we incidentally found a novel oxidative lactonization of 1,6 diols using a catalytic amount of TEMPO and PhI(OAc) 2 as the stoichiometric oxidant. 48,49 To the best of our knowledge, application of these conditions to oxidative lactonization of 1,6 diols to construct seven membered lactones has not been reported. 50 The generality of this oxidative lactonization of 1,6 diols has been evaluated in our laboratory using various substrates and some examples are shown in Table 1.…”

Synthesis ofD-Trigalacturonic Acid Methylglycoside and Conformational Comparison with Its Sulfur Analogue

“…Purification of the residue by silica gel column chromatography (AcOEt:hexane = 25:75) gave 10 (48. 8 (12). A solution of 10 (348 mg, 366 mmol) in 60% aqueous acetic acid solution (8.0 ml) was stirred at 50 C for 20 min.…”

Synthesis, Characterization of Cellulose Grafted N-Oxide Reagent and Its Application in Oxidation of Alkyl/Aryl Halides

“…Efficient methods for the conversion of alcohols to aldehydes, ketones or carboxylic acids under mild conditions have been developed, using TEMPO (2,2,6, 6-tetramethyl-1-piperidinyloxy), (I), as a catalyst and （I） stoichiometric amounts of inexpensive, safe and easy to handle oxidants such as bleach [2], [bis(acetoxy) iodo] benzene (BAIB) [3], trichloroisocyanuricacid (TCCA) [4], oxone [5] or iodine [6].…”