Abstract
Several N-isopropyliodobenzamides were evaluated as catalysts for the oxidation of benzhydrol to benzophenone in the presence of Oxone® (2KHSO5·KHSO4·K2SO4) as a co-oxidant at room temperature. A study on the substituent effect of the benzene ring of N-isopropyl-2-iodobenzamide on the oxidation revealed that its reactivity increased in the following order of substitution: 5-NO2 < 5-CO2Me, 3-OMe < 5-OAc < 5-Cl < H, 4-OMe < 5-Me < 5-OMe. The oxidation of various benzylic and aliphatic alcohols using a catalytic amount of the most reactive 5-methoxy derivative successfully resulted in moderate to excellent yields of the corresponding carbonyl compounds. The high reactivity of the 5-methoxy derivative at room temperature is a result of the rapid generation of the pentavalent species from the trivalent species during the reaction. 5-Methoxy-2-iodobenzamide would be an efficient and environmentally benign catalyst for the oxidation of alcohols, especially benzylic alcohols.
Highlights
The development of an efficient and environmentally benign organic synthesis is required for minimizing material use, energy consumption, and environmental pollution in the production of both bulk and fine chemicals
As part of our study on the development of multifunctionalized organocatalysts based on hypervalent iodine chemistry [60,61,62,63,64,65,66], we found that N-isopropyl-2-iodobenzamide (13), when utilized as a catalyst with Oxone® at room temperature, appears to be a promising catalyst for efficient and environmentally benign alcohol oxidation reactions [67]
We evaluated several 2-iodobenzoic acid derivatives including esters and amides as catalysts for alcohol oxidation in the presence of Oxone®, and we found that the modified derivative, N-isopropylamide 13, exhibited excellent catalytic properties at room temperature [67]
Summary
The development of an efficient and environmentally benign organic synthesis is required for minimizing material use, energy consumption, and environmental pollution in the production of both bulk and fine chemicals. As part of our study on the development of multifunctionalized organocatalysts based on hypervalent iodine chemistry [60,61,62,63,64,65,66], we found that N-isopropyl-2-iodobenzamide (13), when utilized as a catalyst with Oxone® at room temperature, appears to be a promising catalyst for efficient and environmentally benign alcohol oxidation reactions [67].
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