Functionalization of -arylglycine esters: electrocatalytic access to C-C bonds mediated by -BuNI.

Beilstein J Org Chem

Beijing Key Laboratory of Environmental and Viral Oncology, College of Life Science & Bioengineering, Beijing University of Technology, Beijing 100124, China.

Published: February 2018

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.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5827798PMC
http://dx.doi.org/10.3762/bjoc.14.35DOI Listing

Publication Analysis

Top Keywords

functionalization -arylglycine
8
-arylglycine esters
8
esters electrocatalytic
4
electrocatalytic access
4
access c-c
4
c-c bonds
4
bonds mediated
4
mediated -buni
4
-buni efficient
4
efficient electrocatalytic
4

Similar Publications

Photoredox-Catalyzed Sequential Decarboxylative/Defluorinative Aminoalkylation of CF-Alkenes with -Arylglycines.

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 PDF

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 PDF

Photoredox/Enzymatic Catalysis Enabling Redox-Neutral Decarboxylative Asymmetric C-C Coupling for Asymmetric Synthesis of Chiral 1,2-Amino Alcohols.

JACS 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 PDF

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 PDF

Annulation Reaction of Quinoxalin-2(1)-ones Initiated by Electrochemical Decarboxylation of -Arylglycines.

J 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.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!