Metal-free synthesis of secondary amines by the reaction of tosyl triazene and aryl boronic acid

ABSTRACT

A metal free noncatalytic amination process has been developed for the synthesis of N-substituted aniline using a new amine source. The amine source p-toluene sulfonyl triazene (PhN˭NNHTs) has been prepared by treating aryldiazonium salt with p-tosylamide. Various unsymmetrical amines could be synthesized by treating this reagent and boronic acid in toluene at 110 °C in the presence of DBU and 4 Å molecular sieve. A large variety of N-substituted aniline could be synthesized with moderate yield.

GRAPHICAL ABSTRACT

KEYWORDS:

• Amination
• boronic acid
• C–N bond formation
• triazene

Additional information

Funding

Financial support from SERB (DST), India (Grant No. EMR/2016/007883) is gratefully acknowledged.