Dehydrogenative Cross-Coupling Reaction between N-Aryl α-Amino Acid Esters and Phenols or Phenol Derivative for Synthesis of α-Aryl α-Amino 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.

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ChemInform Abstract: Dehydrogenative Cross-Coupling Reaction by Cooperative Transition-Metal and Broensted Acid Catalysis for the Synthesis of β-Quinolinyl α-Amino Acid Esters.

ChemInform ◽

10.1002/chin.201512214 ◽

2015 ◽

Vol 46 (12) ◽

pp. no-no

Author(s):

Zhi-Qiang Zhu ◽

Peng Bai ◽

Zhi-Zhen Huang

Keyword(s):

Amino Acid ◽

Transition Metal ◽

Acid Catalysis ◽

Coupling Reaction ◽

Cross Coupling ◽

Amino Acid Esters ◽

Cross Coupling Reaction ◽

Acid Esters ◽

Cooperative Transition

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Oxidative cross-coupling reaction by scandium catalysis for synthesis of α-alkyl α-amino acid ester derivatives

RSC Advances ◽

10.1039/c7ra00664k ◽

2017 ◽

Vol 7 (27) ◽

pp. 16561-16564 ◽

Cited By ~ 1

Author(s):

Xiao-Hong Wei ◽

Lian-Biao Zhao ◽

Han-Cheng Zhou

Keyword(s):

Amino Acid ◽

Boronic Acid ◽

Acid Ester ◽

Coupling Reaction ◽

Cross Coupling ◽

Amino Acid Ester ◽

Cross Coupling Reaction ◽

Acid Esters

A novel oxidative cross-coupling reaction between N-arylglycine esters and alkyl boronic acid esters was developed by scandium catalysis.

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

Synlett ◽

10.1055/s-0036-1591586 ◽

2018 ◽

Vol 29 (12) ◽

pp. 1659-1663 ◽

Cited By ~ 2

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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Room-Temperature, Water-Promoted, Radical-Coupling Reactions of Phenols with tert-Butyl Nitrite

Synlett ◽

10.1055/s-0036-1589038 ◽

2017 ◽

Vol 28 (16) ◽

pp. 2153-2156 ◽

Cited By ~ 13

Author(s):

Wen-Ting Wei ◽

Hongze Liang ◽

Wen-Ming Zhu ◽

Weida Liang ◽

Yi Wu ◽

...

Keyword(s):

Room Temperature ◽

Coupling Reaction ◽

Cross Coupling ◽

Coupling Reactions ◽

Phenol Derivative ◽

Tert Butyl ◽

Radical Coupling ◽

Air Atmosphere ◽

Cross Coupling Reaction ◽

Temperature Water

A radical–radical cross-coupling reaction of phenols with tert-butyl nitrite has been developed with the use of water as an additive. This method allows the construction of C–N bonds under an air atmosphere at room temperature, providing the ortho-nitrated phenol derivative in moderate to good yields.

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