One‐Pot Synthesis of Symmetrical 1,3‐Diarylureas or Substituted Benzamides Directly from Benzylic Primary Alcohols and Effective Oxidation of Secondary Alcohols to Ketones Using Phenyliodine Diacetate in Combination with Sodium Azide

Abstract

AbstractBenzylic primary alcohols can be directly converted into symmetrical 1,3‐diarylureas or substituted benzamides via an one‐pot oxidative reaction using the combined reagent of phenyliodine diacetate and sodium azide. This new reaction constitutes a step‐economical way to prepare symmetric 1,3‐diarylureas or substituted benzamides depending upon the substituents on the phenyl rings of starting alcohols. The sodium acetate generated in situ from the ligand exchange between phenyliodine diacetate and sodium azide plays the pivotal role in the formation of 1,3‐diarylureas. In addition, it is also found that various secondary alcohols can be readily oxidized to their corresponding ketones in excellent yields using the same reagent system of phenyliodine diacetate and sodium azide. Generally, secondary alcohols are preferentially oxidized to the corresponding ketones in the presence of primary ones with the limited amounts of phenyliodine diacetate and sodium azide.