Synthesis of hydrazines with aromatic substituents using triarylbismuth reagents

Smooth monoarylation of two triprotected hydrazine reagents under mild cond itions has been accomplished using triaryl-bismuthanes in the presence of c opper acetate and amine to give products 3 and 6 in excellent yield. Arylat ion on N-2 after selective deprotection of derivatives with alkyl or aryl s ubstituents on N-1, resulting in compounds 8 and 9, is also demonstrated. F urthermore, other products derived from these reagents with free N-alkyl an d 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 directl y from phenylhydrazine.