Abstract
A protocol for the one-pot synthesis of diarylamines via Smiles rearrangement under microwave irradiation has been developed. Various diarylamines were effectively synthesized starting from readily available substituted phenols, arylamines and chloroacetyl chloride in moderate to good yields (58–92%).
Highlights
Diarylamines represent an important class of compounds due to their wide applications and special pharmacological activities.[1,2] a facile and reliable access to diarylamine derivatives is of great importance
Among numerous methods to prepare diarylamines, the use of metallic catalysts, especially Pd2(dba)[3] and Pd(OAc)[2], is one of the most attractive routes.[3,4,5,6,7,8,9,10]. These metals catalyze the reaction only in the form of metal-organic complexes, which constitute the active catalysts in many C–N bond formation cross-coupling methodologies for the synthesis of diarylamines, while such complexes are quite difficult to prepare and extremely air sensitive.[11]
The limitation of our methodology is that all phenols contain a chlorine atom in ortho position of the phenolic hydroxyl group
Summary
Diarylamines represent an important class of compounds due to their wide applications and special pharmacological activities.[1,2] a facile and reliable access to diarylamine derivatives is of great importance. Wolfe et al.[13] developed a general procedure for the Pd-catalyzed intermolecular amination which proceeds at ambient temperatures, but only aryl iodides can react with a few substituted arylamines in the presence of a strong base like NaOt-Bu. An alternative method of C–N bond formation for the preparation of N-arylamines is the Smiles rearrangement. Our interest in reactions via Smiles rearrangement with two or more reagents being used simultaneously led us to use substituted 2-chlorophenols and arylamines, activated by chloroacetyl chloride for C–N bond formation to obtain diarylamines and arylalkylamines.[19] The limitation of our methodology is that all phenols contain a chlorine atom in ortho position of the phenolic hydroxyl group.
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