149358-58-7Relevant articles and documents
Evidence against an Alternative Mechanism for a Self-Replicating System
Wintner, Edward A.,Tsao, Belinda,Rebek, Julius
, p. 7997 - 8001 (1995)
A recent paper by Menger et al. described experimental and computational work related to our self-replicating system and concluded that amide catalysis - either external or internal - is the cause of observed rate enhancements.Herein we show that the proporsal of Menger et al. is inconsistent with published data, that their conclusions overreach the data afforded by their experiments, and that the step which they modeled is likely irrelevant to the autocatalytic nature of the system.We present new results and a refined mechanism in which the transition state is stabilized not by amides but by template-based recognition, the hallmark of self-replicating systems.
Efficient cleavage of tertiary amide bonds: Via radical-polar crossover using a copper(ii) bromide/Selectfluor hybrid system
Maruoka, Keiji,Matsumoto, Akira,Wang, Zhe
, p. 12323 - 12328 (2020/12/08)
A novel approach for the efficient cleavage of the amide bonds in tertiary amides is reported. Based on the selective radical abstraction of a benzylic hydrogen atom by a CuBr2/Selectfluor hybrid system followed by a selective cleavage of an N-C bond, an acyl fluoride intermediate is formed. This intermediate may then be derivatized in a one-pot fashion. The reaction proceeds under mild conditions and exhibits a broad substrate scope with respect to the tertiary amide moiety as well as to nitrogen, oxygen, and carbon nucleophiles for the subsequent derivatization. Mechanistic studies suggest that the present reaction proceeds via a radical-polar crossover process that involves benzylic carbon radicals generated by the selective radical abstraction of a benzylic hydrogen atom by the CuBr2/Selectfluor hybrid system. Furthermore, a synthetic application of this method for the selective cleavage of peptides is described. This journal is
Nickel-catalyzed reductive amidation of aryl-triazine ethers
Heravi, Majid M.,Panahi, Farhad,Iranpoor, Nasser
supporting information, p. 1992 - 1995 (2020/02/22)
The reaction of activated phenolic compounds, 2,4,6-triaryloxy-1,3,5-triazine (aryl-triazine ethers), with various isocyanates or carbodiimides in the presence of a nickel pre-catalyst resulted in the synthesis of aryl amides in good to excellent yields.
