Copper (I) Catalyzed Sp³ C‐H Arylation of N‐Arylglycine Ester Derivatives under Aerobic Conditions

Abstract

A copper catalyzed cross‐dehydrogenative coupling reaction between N‐arylglycine ester derivatives and 3, 4‐ethylenedioxythiophene or N, N‐dimethylaniline was developed under very mild conditions. This efficient and environmentally benign approach works devoid of additives or external oxidant and delivered various non‐natural‐α‐amino acid derivatives 3 or 5 in moderate to good yields under aerobic condition. High para‐selectivity was observed with N,N‐dialkylaniline functionalizations.

Cross-Dehydrogenative Coupling Reactions for the Functionalization of α-Amino Acid Derivatives and Peptides

“…esters with imidazopyridines, 37 imidazothiazoles, 37 3,4-(ethylenedioxy)thiophene, 38 and N,N-dimethylanilines 38 as the nucleophiles (Figure 1).…”

Thiocyanation of α-amino carbonyl compounds for the synthesis of aromatic thiocyanates

“…Besides, amoxicillin and clopidogrel demonstrate the application of αamino carbonyl compounds in medicine and provide resistance to some diseases. α-Amino carbonyl compounds are involved in many reactions, the most important among which are the reactions with nucleophiles, which include alcohols, 15 thiols, 15 amines, 16,17 phosphites, 18,19 nitromethane, 20 ketones, 21 1,3-dicarbonyl compounds, [22][23][24] (hetero) arenes, [25][26][27][28][29][30][31] and others.…”

Copper‐Catalyzed Double Friedel‐Crafts Alkylation of Tetrahydroquinolines Under Aqueous Conditions: Efficient Synthesis of gem‐Diarylacetic Esters

“…We have previously demonstrated the copper‐catalyzed α‐arylation, amidation/imidation of N ‐arylglycine esters under mild conditions. Tetrahydroquinolines (THQs) belong to a class of heterocycles of high pharmacological value and in general organic reactions in water as solvent attracted tremendous interest over other organic solvents due to its green and environmentally benign nature .…”