Direct NHC-catalysed redox amidation using CO2 for traceless masking of amine nucleophiles.
نویسندگان
چکیده
The N-heterocyclic carbene (NHC)-catalysed redox amidation reaction is poorly developed and usually requires catalytic co-additives for electron-rich amine nucleophiles. We report a masking strategy (using CO2) that couples release of the free amine nucleophile to catalytic turnover, and in doing so, enables direct catalytic redox amidation of electron-rich amines.
منابع مشابه
Rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes: effective conversion of amines and anilines into amides
The rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes is reported. In situ generated [(BINAP)Rh]BF4 catalyzes the one-pot isomerization/oxidative amidation of allylic alcohols or direct amidation of aldehydes using acetone or styrene as the hydrogen acceptor. The conditions are general, affording good to excellent yields with a wide array of amine and aniline nucleophiles,...
متن کاملα-Aroyloxyaldehydes: scope and limitations as alternatives to α-haloaldehydes for NHC-catalysed redox transformations.
α-Aroyloxyaldehydes are readily prepared bench stable synthetic intermediates. Their ability to act as α-haloaldehyde surrogates for NHC-promoted redox esterifications and in [4+2] cycloadditions is described.
متن کاملNew palladium catalysed reactions of bromoporphyrins: synthesis and crystal structures of nickel(II) complexes of primary 5-aminoporphyrin, 5,59-bis(porphyrinyl) secondary amine, and 5-hydroxyporphyrin{
Palladium catalysed coupling reactions on haloporphyrins have revolutionised the functionalisation of the porphyrin periphery. There are now many and varied examples of successful C–C and C–X couplings, expecially on the meso positions(s) of 5,15-diarylor 5,10,15-triarylporphyrins, to produce a range of functionalised mononuclear derivatives, as well as diand oligonuclear arrays with alkynyl, a...
متن کاملDirect amidation of non-activated phenylacetic acid and benzylamine derivatives catalysed by NiCl2
This paper describes an eco-friendly and efficient direct amidation of benzylamine and phenylacetic acid derivatives in the presence of 10 mol% NiCl2 as catalyst without any drying agent. For the different phenylacetic acid and benzylamine derivatives, the direct catalysed amidation gave moderate-to-excellent yields in toluene. The steric and electronic effects of substituent groups on the phen...
متن کاملSterically Demanding Oxidative Amidation of α‐Substituted Malononitriles with Amines Using O2
An efficient amidation method between readily available 1,1-dicyanoalkanes and either chiral or nonchiral amines was realized simply with molecular oxygen and a carbonate base. This oxidative protocol can be applied to both sterically and electronically challenging substrates in a highly chemoselective, practical, and rapid manner. The use of cyclopropyl and thioether substrates support the rad...
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:
- Chemical communications
دوره 52 78 شماره
صفحات -
تاریخ انتشار 2016