Oxidative amidation and azidation of aldehydes by NHC catalysis.
نویسندگان
چکیده
N-heterocyclic carbene catalyzed oxidative amidations of various aldehydes to the corresponding hexafluoroisopropylesters by using the readily available organic oxidant A are described. The hexafluoroisopropylesters prepared in situ are shown to be highly useful active esters for amide bond formation. In addition, oxidative azidation of aldehydes is presented. These mild organocatalytic processes do not use any transition metal.
منابع مشابه
NHC/iron cooperative catalysis: aerobic oxidative esterification of aldehydes with phenols.
An NHC/iron cooperative catalytic system mediates the aerobic oxidative esterification of aldehydes with phenols. The use of equimolar amounts of reactants led to good to excellent isolated yields of esters.
متن کاملDirect α-functionalization of simple aldehydes via oxidative N-heterocyclic carbene catalysis.
A direct α-functionalization of simple aldehydes under N-Heterocyclic Carbene (NHC) catalysis and direct generation of ester enolate equivalents from nonfunctionalized aldehydes are disclosed. The catalysis involves selective enolate generation from an oxidatively generated NHC-bounded ester intermediate as a key step. The ester enolate intermediates undergo stereoselective reactions with enone...
متن کاملDirect oxidative amidation of aldehydes with amines catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions via a dual-catalysis process.
A simple and efficient procedure for the synthesis of amides directly from aldehydes and amines catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions has been reported. The practical protocol was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, solvent-free media, and operational simplicity are the main highlig...
متن کاملN-heterocyclic-carbene-catalyzed asymmetric oxidative hetero-Diels-Alder reactions with simple aliphatic aldehydes.
N-heterocyclic carbene (NHC) catalysis has emerged as a powerful tool for synthesis. Among its involvement in several cycloaddition-type reactions for the construction of lactams and lactones, which are abundant in biologically active molecules and broadly used as synthons for complex molecules, NHC catalysis through formal [3+3] or [4+2] strategies is noteworthy. In particular, [4+2] cycloaddi...
متن کاملOxidative N-heterocyclic carbene catalyzed stereoselective annulation of simple aldehydes and 5-alkenyl thiazolones.
A highly diastereoselective annulation of simple aldehydes and 5-alkenyl thiazolones, via oxidative NHC catalysis has been developed. This strategy provides facile access to a diverse library of functionalized chiral thiazolo pyrones. Aerobic oxygen can also be applied as a secondary oxidant to avoid the use of stoichiometric organic or inorganic oxidants.
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:
- Organic letters
دوره 12 9 شماره
صفحات -
تاریخ انتشار 2010