Silver-catalyzed nitrosation and nitration of aromatic amides using NOBF₄

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Catalysis

Background:

• Aromatic amides are versatile building blocks in organic synthesis.
• Selective functionalization of aromatic rings remains a key challenge.
• Nitrosation and nitration are important transformations for modifying aromatic compounds.

Purpose of the Study:

• To develop a novel synthetic methodology for the divergent functionalization of aromatic amides.
• To explore the use of NOBF4 as an electrophile in silver-catalyzed reactions.
• To achieve regioselective ortho-nitrosation, deacylation-nitrosation, and nitration of aromatic amides.

Main Methods:

• Utilizing NOBF4 as the electrophile.
• Employing silver catalysis to promote the reactions.
• Investigating the reactivity of various tertiary and secondary aromatic amides.

Main Results:

• Efficient divergent aromatic ring nitrosation and nitration were achieved.
• The method provides regioselective ortho-nitrosation products.
• Deacylation nitrosation products and nitration products were also obtained.
• The reactions demonstrated compatibility with a wide range of functionalities.

Conclusions:

• A novel and efficient silver-catalyzed method for aromatic amide functionalization has been established.
• The methodology allows for divergent synthesis of nitrosated and nitrated aromatic amides.
• This work expands the synthetic toolbox for accessing valuable aromatic compounds.