183198-63-2Relevant articles and documents
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
Highly Efficient Copper-Catalyzed Amidation of Benzylic Hydrocarbons Under Neutral Conditions
Howard, Eva-Louise,Guzzardi, Norman,Tsanova, Viliyana G.,Stika, Angeliki,Patel, Bhaven
supporting information, p. 794 - 797 (2018/02/21)
A ligand free method has been developed for the amidation of benzylic hydrocarbons. A range of benzylic amides has been prepared with the use of dicumyl peroxide and a copper catalyst in good to excellent yields.
Repurposing n-butyl stannoic acid as highly efficient catalyst for direct amidation of carboxylic acids with amines
Potadar, Santoshkumar M.,Mali, Anil S.,Waghmode, Krishnakant T.,Chaturbhuj, Ganesh U.
supporting information, p. 4582 - 4586 (2018/11/27)
This is the first-time report on the repurposing n-butyl stannoic acid as a catalyst for direct amidation of carboxylic acids with amines. Notably, efficient amidation observed in comparison with all other catalytic methods reported up until now. The protocol has successfully applied to the synthesis of a variety of amides. Moderate reaction parameters, clean amidation with excellent yields of desired amides, ability to tolerate a variety of functional groups, easy product isolation; commercial availability and recyclability of the catalyst are key advantages of the current protocol.