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New synthetic “tricks”. Triphenylphosphine-mediated amide formation from carboxylic acids and azides

✍ Scribed by Jordi Garcia; Fèlix Urpí; Jaume Vilarrasa

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
273 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis

Equimolar amounts of carboxylic acids, aryl or alkyl azides, and Ph3P in refluxing benzene (hexane, toluene) afford amides in good yields. Insolubility of zwitterions Ph3&NH(CH2),COO', arising from w-azido acids and Ph3P, limits the utilization of the method for loctame formation. A plethora of phosphorus derivatives have been used to obtain amides from carboxylic acids and amines under mi Id conditions: Ph3P plus CC14, Ph3P(OR)2, R2P(=O)X, pol t ys yryldiphenylphosphine plus CC14, Ph3P plus py-S-S-py or other disulphides, Palomo's P-oxazolidone derivative, Ru3P plus o-CoH4(NO2)X, etc. 1 Some of -

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A new type of amide formation from thioc
A new type of amide formation from thiocarboxylic acid and alkyl azide
✍ Sang-Don Park; Jung-Hee Oh; Dongyeol Lim 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 61 KB

We studied the coupling of thiocarboxylic acid and alkyl azide using various triaryl phosphines. Amide formation greater than 95% was achieved when the free-formation of Staudinger intermediate with electron deficient triaryl phosphines was employed.