22795-70-6

Upstream product

• 529-20-4 2-methylphenyl aldehyde 
• 89-95-2 2-methyl-benzyl alcohol 
• 4648-54-8 trimethylsilylazide 
• 95-46-5 2-methylphenyl bromide 
• 50978-45-5 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide 
• 147501-26-6 methyl 3-oxo-3-(o-tolyl) propanoate 

Relevant academic research and scientific papers

Radical Azidonation of Aldehydes

Aliphatic and aromatic aldehydes can be converted to acyl azides by treatment with iodine azide at 0-25°C. If the reaction is performed at reflux Curtius rearrangement occurs and carbamoyl azides are obtained in 70-97% yield from the aldehyde. The reaction was shown to have a radical mechanism.

Copper-Catalyzed Nitrogenation of Aromatic and Aliphatic Aldehydes: A Direct Route to Carbamoyl Azides

An efficient copper-catalyzed synthesis of carbamoyl azides directly from aldehydes has been developed. Both aromatic aldehydes and aliphatic aldehydes, together with other commercially available reactants, can be used as substrates in this radical relay reaction. Broad substrate scope, simple operation, readily available reagents, and good functionality tolerance make this method very attractive.

KI Catalyzed Nitrogenation of Aldehydes and Alcohols: Direct Synthesis of Carbamoyl Azides and Ureas

An efficient KI catalyzed nitrogenation of aldehydes and alcohols for the direct synthesis of carbamoyl azides and ureas via a radical process has been developed. The simple operating procedures, the readily available starting materials including aldehydes, alcohols and amines, as well as the utility of the products all make this strategy very attractive.

One-Pot Synthesis of Carbamoyl Azides via Palladium-Catalysed Azidocarbonylation of Haloarenes Using N-Formylsaccharin as a CO Surrogate

A highly efficient one-pot synthesis of carbamoyl azides from haloarenes and sodium azide has been developed. The protocol involves palladium-catalysed azidocarbonylation of haloarenes utilizing N-formylsaccharin as a CO source to form acyl azides, which undergo in situ Curtius rearrangement to afford the desired carbamoyl azides. N-Formylsaccharin is an easy-to-handle solid alternative to CO gas.

Ceric ammonium nitrate (CAN) catalyzed modification of ketones via two C-C bond cleavages with the retention of the oxo-group

A simple ceric ammonium nitrate (CAN) catalyzed functionalization of ketones through double C-C bond cleavage strategy has been disclosed. This reaction provides a mild, practical method toward carbamoyl azides, which are versatile intermediates and building blocks in organic synthesis. Based on relevant mechanistic studies, a unique and plausible C-C bond and N-O bond cleavage process is proposed, where the oxyamination intermediate plays an important role in this reaction.

One-pot synthesis of carbamoyl azides directly from primary alcohols and oxidation of secondary alcohols to ketones using iodobenzene dichloride in combination with sodium azide

An effective synthesis of carbamoyl azides directly from primary alcohols using iodobenzene dichloride in combination with sodium azide has been developed. Moreover, the same regent combination was also efficient for the oxidation of secondary alcohols to the corresponding ketones.