A Highly Efficient Copper(II)-Catalyzed Cross-Dehydrogenative-Coupling Reaction of N-Arylglycine Esters with 2-Arylimidazo[1,2-a]pyridines

Synthesis ◽  
2018 ◽  
Vol 50 (14) ◽  
pp. 2775-2783 ◽  
Author(s):  
Zhi-Qiang Zhu ◽  
Zhang-Gao Le ◽  
Li-Jin Xiao ◽  
Ying Chen ◽  
Zong-Bo Xie ◽  
...  
Keyword(s):  
Amino Acid ◽  
Functional Groups ◽  
Coupling Reaction ◽  
Amino Acid Esters ◽  
Synthetic Method ◽  
Reaction Conditions ◽  
Highly Efficient ◽  
Dehydrogenative Coupling ◽  
High Yields ◽  
Acid Esters

A rapid and highly efficient copper(II)-catalyzed cross-dehydrogenative coupling (CDC) reaction of N-arylglycine esters with imidazo[1,2-a]pyridines has been described. A broad range of N-arylglycine esters underwent the CDC reaction smoothly with 2-arylimidazo[1,2-a]pyridines to give α-substituted α-amino acid esters in excellent yields. This synthetic method has the advantages of high yields, good functional groups compatibility, simple operation, and mild reaction conditions. A possible mechanism for the CDC reaction is also proposed. The use of a copper salt as the catalyst and air as the terminal oxidant makes this transformation sustainable and practical.

Copper-Catalyzed Cross-Dehydrogenative-Coupling Reaction of N-Arylglycine Esters with Imides or Amides for Synthesis of α-Substituted α-Amino Acid Esters

Synlett ◽  
2018 ◽  
Vol 29 (12) ◽  
pp. 1659-1663 ◽  
Author(s):  
Zhi-Qiang Zhu ◽  
Zong-Bo Xie ◽  
Zhang-Gao Le ◽  
Li-Jin Xiao ◽  
Dong Guo ◽  
...  
Keyword(s):  
Amino Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Synthetic Approach ◽  
Amino Acid Esters ◽  
The Novel ◽  
Reaction Conditions ◽  
Simple Operation ◽  
Dehydrogenative Coupling ◽  
Acid Esters

A simple and highly efficient cross-dehydrogenative-­coupling (CDC) reaction between N-aryl glycine esters and imides or amides by the catalysis of a copper salt without the requirement of ­peroxide agents is described. The novel reaction provides a facile ­approach for the synthesis of α-substituted α-amino acid esters through C–H/N–H oxidative cross-coupling. A possible mechanism for the CDC reaction by using copper as a catalyst and air as the terminal oxidant is also proposed. This synthetic approach has the advantages of good yields, simple operation and mild reaction conditions.

Metallkomplexe von Biologisch Wichtigen Liganden, CXLVIII [1]. Katalytische Peptidsynthese aus Glycinester miit Hilfe von Triflaten Und Cloriden der Seltenen Erden, sowie von Metall(III), (IV), (V) und (VI)-Chloriden / Metal Complexes of Biologically Important Ligands, CXLVIII [1]. Synthesis of Peptides from Glycine Ester Catalysed by Triflates and Chlorides of Metal(III, IV, V And VI) Ions

2003 ◽  
Vol 58 (1) ◽  
pp. 85-91 ◽  
Author(s):  
Jan Schapp ◽  
Wolfgang Beck
Keyword(s):  
Amino Acid ◽  
Metal Complexes ◽  
Dansyl Chloride ◽  
Amino Acid Esters ◽  
Metal Chlorides ◽  
Peptide Formation ◽  
Metal Triflates ◽  
High Yields ◽  
Acid Esters

Abstract Formation of di- and triglycine ethylester which were determined by HPLC after derivatisation with dansyl chloride was observed in medium to high yields from CH2Cl2 solutions of glycine ethylester in the presence of metal triflates and metal chlorides: FeCl3 (yield 82%), AlCl3 (73%), GdCl3 (56%), La(OTf)3 (59%), Sc(OTf)3 (55%), ZrCl4 (62%), HfCl4 (60%), VOCl3 (43%), TaCl5 (29%). Esters of higher α-amino acid esters (AlaOMe, PheOMe) gave lower yields in peptide formation.

scholarly journals Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols

2012 ◽  
Vol 8 ◽  
pp. 2004-2018 ◽  
Author(s):  
Rajendra Surasani ◽  
Dipak Kalita ◽  
A V Dhanunjaya Rao ◽  
K B Chandrasekhar
Keyword(s):  
Amino Acid ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Amino Acid Esters ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Acid Esters

Simple and efficient procedures for palladium-catalyzed cross-coupling reactions of N-substituted 4-bromo-7-azaindole (1H-pyrrole[2,3-b]pyridine), with amides, amines, amino acid esters and phenols through C–N and C–O bond formation have been developed. The C–N cross-coupling reaction of amides, amines and amino acid esters takes place rapidly by using the combination of Xantphos, Cs2CO3, dioxane and palladium catalyst precursors Pd(OAc)2/Pd2(dba)3. The combination of Pd(OAc)2, Xantphos, K2CO3 and dioxane was found to be crucial for the C–O cross-coupling reaction. This is the first report on coupling of amides, amino acid esters and phenols with N-protected 4-bromo-7-azaindole derivatives.

Highly Efficient Copper-Catalyzed Dehydrogenative Cross-Coupling of Azoles and α-Amino Carbonyl Compounds

Synthesis ◽  
2020 ◽  
Author(s):  
Jiu-Jian Ji ◽  
Zhi-Qiang Zhu ◽  
Zong-Bo Xie ◽  
Juan Tang ◽  
En Yuan ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Functional Group ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Synthetic Method ◽  
Diverse Range ◽  
Highly Efficient ◽  
Cross Coupling Reaction ◽  
Butyl Peroxide ◽  
High Yields

A novel and highly efficient dehydrogenative cross-coupling reaction between α-amino carbonyl compounds and azoles by copper catalysis using di-tert-butyl peroxide (DTBP) as an oxidant was described. A diverse range of azoles underwent the dehydrogenative imidoylation smoothly with various α-amino carbonyl compounds for the exclusive formation of the corresponding N-imidoyl azoles in high yields under air. The synthetic method has the advantages of good functional-group tolerance, wide substrate scope, excellent yields and simple operation, thus providing a convenient and practical protocol for the synthesis of various functionalized azoles.

Transition-Metal-Free Synthesis of Trifluoromethylated Furans via a Bu3P-Mediated Tandem Acylation–Wittig Reaction

Synlett ◽  
2020 ◽  
Vol 31 (20) ◽  
pp. 2035-2038
Author(s):  
Wei Zhou ◽  
Maizhan Li
Keyword(s):  
Transition Metal ◽  
Functional Groups ◽  
Nucleophilic Addition ◽  
Wittig Reaction ◽  
Reaction Conditions ◽  
Metal Free ◽  
Highly Efficient ◽  
Intramolecular Wittig Reaction ◽  
High Yields

AbstractA highly efficient nucleophilic addition–O-acylation–intramolecular Wittig reaction of β-trifluoromethyl α,β-enones is disclosed. This strategy features mild reaction conditions and provides a practical transition-metal-free method to a set of biologically significant trifluoromethylated furans in high yields with diverse functional groups.

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