Amide synthesis by nucleophilic attack of vinyl azides.
نویسندگان
چکیده
A method for the synthesis of amide-containing molecules was developed using vinyl azides as an enamine-type nucleophile towards carbon electrophiles, such as imines, aldehydes, and carbocations that were generated from alcohols in the presence of BF3 ⋅OEt2 . After nucleophilic attack of the vinyl azide, a substituent of the resulting iminodiazonium ion intermediate migrates to form a nitrilium ion, which is hydrolyzed to afford the corresponding amide.
منابع مشابه
Phosphine-based redox catalysis in the direct traceless Staudinger ligation of carboxylic acids and azides.
The synthesis of amide C N bonds through nucleophilic acyl substitutions constitutes one of the most fundamental transformations in chemical synthesis. Recently, the Staudingertype ligation of carboxylic acid derivatives (e.g., acid chlorides, anhydrides, acyl selenides, and thioesters) and azides has become a preeminent strategy for amide C N bond construction (Scheme 1a). However, the generat...
متن کاملContinuous multistep synthesis of 2-(azidomethyl)oxazoles
An efficient three-step protocol was developed to produce 2-(azidomethyl)oxazoles from vinyl azides in a continuous-flow process. The general synthetic strategy involves a thermolysis of vinyl azides to generate azirines, which react with bromoacetyl bromide to provide 2-(bromomethyl)oxazoles. The latter compounds are versatile building blocks for nucleophilic displacement reactions as demonstr...
متن کاملPorous Acidic Catalyst, Functionalized with Imidazole Ionic Liquid ([SBA-Im]HSO4) as a Novel Phase Transfer Catalyst for The Aqueous Synthesis of Benzyl Thiocyanates and Azides
In the present study, application of porous acidic catalyst functionalized with an imidazoleionic liquid ([SBA-Im]HSO4) as a phase transfer catalyst for the facile preparation of benzylthiocyanates and azides in water has been described. The catalyst has been characterized byFourier transform infrared spectroscopy (FT-IR), scanning electron microscope (SEM), transmissionelectron microscopy (TEM...
متن کاملMultistep flow synthesis of vinyl azides and their use in the copper-catalyzed Huisgen-type cycloaddition under inductive-heating conditions
The multistep flow synthesis of vinyl azides and their application in the synthesis of vinyltriazoles is reported. The synthesis relies on a stable polymer-bound equivalent of iodine azide that serves to carry out 1,2-functionalization of alkenes in a telescope flow protocol. The intermediate 2-iodo azides are subjected to a DBU-mediated polymer-supported elimination step yielding vinyl azides ...
متن کاملMn(III)-catalyzed radical reactions of 1,3-dicarbonyl compounds and cyclopropanols with vinyl azides for divergent synthesis of azaheterocycles.
Mn(III)-catalyzed formal [3+2]- and [3+3]-annulations have been developed using readily available vinyl azides with 1,3-dicarbonyl compounds and cyclopropanols. Vinyl azides were successfully applied as a three-atom unit including one nitrogen to prepare various azaheterocycles via Mn(III)-catalyzed radical reactions.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Angewandte Chemie
دوره 53 17 شماره
صفحات -
تاریخ انتشار 2014