6004-95-1Relevant academic research and scientific papers
A Hydroperoxide-Mediated Decarboxylation of α-Ketoacids Enables the Chemoselective Acylation of Amines
Nanjo, Takeshi,Kato, Natsuki,Zhang, Xuan,Takemoto, Yoshiji
supporting information, p. 15504 - 15507 (2019/11/14)
Strategies for the formation of amide bonds, that is, one of the most basic and important transformations in organic synthesis, have so far focused predominantly on dehydration reactions. Herein, we report and demonstrate the practical utility of a novel decarboxylative amidation of α-ketoacids by using inexpensive tert-butyl hydroperoxide (TBHP), which is characterized by high yields, a broad substrate scope, mild reaction conditions, and a unique chemoselectivity. These features enable the synthesis of peptides from amino acid derived α-ketoacids under preservation of the stereochemical information.
A Practical and General Amidation Method from Isocyanates Enabled by Flow Technology
Williams, Jason D.,Kerr, William J.,Leach, Stuart G.,Lindsay, David M.
supporting information, p. 12126 - 12130 (2018/09/11)
The addition of carbon nucleophiles to isocyanates represents a conceptually flexible and efficient approach to the preparation of amides. This general synthetic strategy has, however, been relatively underutilized owing to narrow substrate tolerance and the requirement for less favourable reaction conditions. Herein, we disclose a high-yielding, mass-efficient, and scalable method with appreciable functional group tolerance for the formation of amides by reaction of Grignard reagents with isocyanates. Through the application of flow chemistry and the use of substoichiometric amounts of CuBr2, this process has been developed to encompass a broad range of substrates, including reactants found to be incompatible with previously published procedures.
Facile direct synthesis of amides from trichloroethyl esters using catalytic DBU
La, Minh Thanh,Kim, Hee-Kwon
, p. 1135 - 1141 (2018/11/25)
A practical method for the direct synthesis of amide compounds is described. Using small quantities of DBU as a catalyst, the direct conversion of 2,2,2-trichloroethyl esters to their corresponding amides was readily achieved. Based on this protocol, various amide compounds were successfully synthesized in high yield, suggesting a promising approach for the practical one-pot aminolysis from 2,2,2-trichloroethyl protected esters.
Rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes: Effective conversion of amines and anilines into amides
Wu, Zhao,Hull, Kami L.
, p. 969 - 975 (2016/02/05)
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, and chemoselective, other alcohols do not participate in the oxidation reaction. Utilization of biphasic conditions is critical, as they promote an equilibrium between the imine/enamine byproducts and the hemiaminal, which can undergo oxidation to the amide.
Ruthenium-catalysed oxidation of alcohols to amides using a hydrogen acceptor
Watson, Andrew J.A.,Wakeham, Russell J.,Maxwell, Aoife C.,Williams, Jonathan M.J.
supporting information, p. 3683 - 3690 (2014/05/20)
A wider investigation into the synthesis of secondary amides from primary alcohols using a hydrogen acceptor using commercially available [Ru(p-cymene)Cl2]2 with bis(diphenylphosphino)butane (dppb) as the catalyst. The report looks at over 50 examples with varying functionality and steric bulk, whilst also covering the first reported results using microwave heating to effect the transformation.
