Unexpected C-C bond cleavage of α-nitroketone in the presence of TsNBr₂: A new pathway for C-N bond formation

ABSTRACT

A new catalyst-free protocol for C-N bond formation via the cleavage of α-nitroketone has been developed. When α -nitroketones are treated with TsNBr₂ in the presence of potassium carbonate, unexpected cleavage of C(O)-CHNO₂ bond of α -nitroketone was observed followed by the formation of corresponding amide. Various nitroketones could be converted to corresponding amide using this procedure.

GRAPHICAL ABSTRACT

KEYWORDS:

• Amide
• C-C bond cleavage
• C-N bond formation
• α-nitroketone
• TsNBr₂

Additional information

Funding

Financial support from the Department of Science and Technology (DST), India (Grant No. SR/S1/OC-43/2011), is gratefully acknowledged.