An efficient electrocatalytic functionalization of -arylglycine esters is reported. The protocol proceeds in an undivided cell under constant current conditions employing the simple, cheap and readily available -BuNI as the mediator. In addition, it is demonstrated that the mediated process is superior to the direct electrochemical functionalization.
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http://dx.doi.org/10.3762/bjoc.14.35 | DOI Listing |
Org Lett
July 2024
Department of Chemistry, School of Chemistry, Xi'an Key Laboratory of Sustainable Energy Material Chemistry and Engineering Research Center of Energy Storage Materials and Devices, Ministry of Education, Xi'an Jiaotong University, Xi'an 710049, China.
A photoredox-catalyzed sequential decarboxylative/defluorinative aminoalkylation of CF-alkenes with -arylglycines is described. This metal-free and redox-neutral protocol provided efficient access to the monofluoroalkenyl-1,5-diamines in good yields with excellent functional group compatibility. Mechanistic studies revealed that the reaction proceeds via a radical pathway with the -difluoroalkenyl amine as an intermediate.
View Article and Find Full Text PDFJ Org Chem
July 2024
Department of Chemistry, Moscow State University, Moscow 119991, Russia.
Diethyl acetamidomalonate (DEAM) has been widely used for the synthesis of α-amino acids via C-alkylation under basic conditions followed by hydrolysis/decarboxylation. In contrast, the C-arylation of this reagent remains undeveloped. Herein, we report a novel strategy for the synthesis of racemic α-arylglycines based on the selective arylation of DEAM with diaryliodonium salts under mild, transition metal-free conditions.
View Article and Find Full Text PDFJACS Au
November 2023
National Engineering Research Center of Industrial Enzymes and Tianjin Engineering Research Center of Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, Tianjin 300308, China.
Photocatalysis offers tremendous opportunities for enzymes to access new functions. Herein, we described a redox-neutral photocatalysis/enzymatic catalysis system for the asymmetric synthesis of chiral 1,2-amino alcohols via decarboxylative radical C-C coupling of -arylglycines and aldehydes by combining an organic photocatalyst, eosin Y, and carbonyl reductase RasADH. Notably, this protocol avoids using any sacrificial reductants.
View Article and Find Full Text PDFOrg Lett
October 2023
Biophamaceutical Research Institute, West China Hospital, Sichuan University, 37 Guoxue Alley, Chengdu 610041, China.
A novel copper-catalyzed cross-dehydrogenative-coupling (CDC) process of arylglycine derivatives with N-heteroarenes for the straightforward synthesis of α-aryl-α-heteroaryl α-amino acid scaffolds has been successfully developed. This protocol exhibits a broad substrate scope with good functional group compatibility by utilizing air as the sole oxidant. The use of the reaction is also displayed through the late-stage functionalization of arylglycines bearing natural compounds or drug motifs.
View Article and Find Full Text PDFJ Org Chem
January 2023
Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong 510640, China.
A new methodology for the synthesis of tetrahydroimidazo[1,5-]quinoxalin-4(5)-ones has been accomplished through annulation of quinoxalin-2(1)-ones initiated by electrochemical decarboxylation of -arylglycines catalyzed by ferrocene. With a pair of oxidative and reductive processes occurring among the substrates and intermediates instead of on the electrodes, the electricity consumption was decreased.
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