82342-56-1Relevant articles and documents
Generation of Oxyphosphonium Ions by Photoredox/Cobaloxime Catalysis for Scalable Amide and Peptide Synthesis in Batch and Continuous-Flow
Chen, Xiangyang,Houk, Kendall N.,Mo, Jia-Nan,Su, Junqi,Umanzor, Alexander,Zhang, Zheng,Zhao, Jiannan
supporting information, (2022/01/06)
Phosphine-mediated deoxygenative nucleophilic substitutions, such as the Mitsunobu reaction, are of great importance in organic synthesis. However, the conventional protocols require stoichiometric oxidants to trigger the formation of the oxyphosphonium i
Catalytic N-Acylation of Cyclic Amines by Arylglyoxylic Acids via Radical-Radical Cross-Coupling
Bhadra, Sukalyan,Gupta, Aniket,Kumar Singh, Anupam,Rahaman, Ajijur
supporting information, p. 2198 - 2202 (2021/07/22)
A methodical mechanistic investigation allowed for the catalytic N-acylation of secondary cyclic amine counterparts by arylglyoxylic acids through radical-radical coupling. The reaction proceeds via a twofold SET-promoted Cu(I)/Cu(II) catalytic cycle under mild conditions. An analogous reaction variant allows for the N-acylation in a one-pot fashion directly starting from a secondary cyclic amine even in the presence of a second amine or hydroxy group.
Nickel-Catalyzed Amide Bond Formation from Methyl Esters
Ben Halima, Taoufik,Masson-Makdissi, Jeanne,Newman, Stephen G.
supporting information, p. 12925 - 12929 (2018/09/14)
Despite being one of the most important and frequently run chemical reactions, the synthesis of amide bonds is accomplished primarily by wasteful methods that proceed by stoichiometric activation of one of the starting materials. We report a nickel-catalyzed procedure that can enable diverse amides to be synthesized from abundant methyl ester starting materials, producing only volatile alcohol as a stoichiometric waste product. In contrast to acid- and base-mediated amidations, the reaction is proposed to proceed by a neutral cross coupling-type mechanism, opening up new opportunities for direct, efficient, chemoselective synthesis.