Radical-Coupling Reaction for the Synthesis of γ-Amino Acid Esters

Synfacts ◽  
2021 ◽  
Vol 17 (11) ◽  
pp. 1286
Keyword(s):  
Amino Acid ◽  
Coupling Reaction ◽  
Amino Acid Esters ◽  
Radical Coupling ◽  
Radical Coupling Reaction ◽  
Acid Esters

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.

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.

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