Synthesis of Hydrazines with Aromatic Substituents Using Triarylbismuth Reagents

Smooth monoarylation of two triprotected hydrazine reagents under mild conditions has been accomplished using triarylbismuthanes in the presence of copper acetate and amine to give products 3 and 6 in excellent yield. Arylation on N ² after selective deprotection of derivatives with alkyl or aryl substituents on N ¹, resulting in compounds 8 and 9, is also demonstrated. Furthermore, other products derived from these reagents with free N-alkyl and N-aryl functions undergo the same reaction to give substances such as 10 and 11. As a result, the scope of the original hydrazine reagents has been further extended. A few reference compounds have also been prepared directly from phenylhydrazine.

N-arylations - arylbismuthanes - multisubstituted hydrazines - organometallic reagents - stepwise synthesis