While arylazo sulfones have been widely applied as arylating agents, their exploitation for diazenylation reactions has been previously limited to electron-rich alkenes such as styrenes and silyl enol ethers. Herein we optimized a synthetic one-pot protocol to access oxazolyl azo compounds via a selective domino ring-closing/aryldiazenylation sequence by starting from arylazo sulfones and isocyanoacetamides in the presence of Sm(OTf)3 as the Lewis acid. The substrate scope, along with scale-up reaction both in batch and under continuous flow conditions provide a valuable approach to such a class of heteroaryl azo compounds.
Dual Lewis Acid Promoted/Visible Light Driven Preparation of Aryl Diazenyl Oxazoles from Isocyanoacetamides and Arylazo Sulfones
di Terlizzi, Lorenzo;Protti, Stefano
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In corso di stampa
Abstract
While arylazo sulfones have been widely applied as arylating agents, their exploitation for diazenylation reactions has been previously limited to electron-rich alkenes such as styrenes and silyl enol ethers. Herein we optimized a synthetic one-pot protocol to access oxazolyl azo compounds via a selective domino ring-closing/aryldiazenylation sequence by starting from arylazo sulfones and isocyanoacetamides in the presence of Sm(OTf)3 as the Lewis acid. The substrate scope, along with scale-up reaction both in batch and under continuous flow conditions provide a valuable approach to such a class of heteroaryl azo compounds.File in questo prodotto:
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