Dehydrogenative Cross-Coupling Reactions of N-Aryl α-Amino Acid Esters with Nitroalkanes for the Synthesis of β-Nitro 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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Dehydrogenative Cross-Coupling Reaction by Cooperative Transition-Metal and Brønsted Acid Catalysis for the Synthesis of β-Quinolinyl α-Amino Acid Esters

Organic Letters ◽

10.1021/ol502402s ◽

2014 ◽

Vol 16 (18) ◽

pp. 4881-4883 ◽

Cited By ~ 68

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 ◽

Brönsted Acid ◽

Acid Esters ◽

Cooperative Transition

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Visible-light-induced iodine anion catalyzed decarboxylative/ deaminative C-H alkylation of enamides

Organic Chemistry Frontiers ◽

10.1039/d1qo00660f ◽

2021 ◽

Author(s):

Jia-Xin Wang ◽

Ya-Ting Wang ◽

Hao Zhang ◽

Ming-Chen Fu

Keyword(s):

Amino Acid ◽

Visible Light ◽

Cross Coupling ◽

Coupling Reactions ◽

Active Esters ◽

Cross Coupling Reactions ◽

Redox Active ◽

Iodine Anion

A visible-light-induced iodine anion catalyzed C-H stereoselective alkylation of enamides has been developed. Redox-active esters and Katritzky salts of the amino acid are amenable for decarboxylative/deaminative cross-coupling reactions, delivering various...

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Synthetic studies of novel ninhydrin analogs

Canadian Journal of Chemistry ◽

10.1139/v01-143 ◽

2001 ◽

Vol 79 (11) ◽

pp. 1632-1654 ◽

Cited By ~ 18

Author(s):

Richard R Hark ◽

Diane B Hauze ◽

Olga Petrovskaia ◽

Madeleine M Joullié

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Cross Coupling ◽

Coupling Reactions ◽

Latent Fingerprints ◽

Cross Coupling Reactions ◽

Essential Tool ◽

Porous Surfaces ◽

Synthetic Studies ◽

Sulfur Containing

Ninhydrin is an essential tool in the analysis of amino acids, peptides, and proteins, and the preferred reagent for the detection of latent fingerprints on porous surfaces. The goal of this investigation was to prepare ninhydrin analogs with enhanced chromogenic and fluorogenic properties. Target compounds included structures with extended conjugation and (or) with the presence of sulfur-containing moieties. We have devised general convergent routes for novel heterocyclic and aryl-substituted ninhydrin analogs for use as reagents for amino acid detection.Key words: ninhydrin analogs, synthesis, ketals, Suzuki cross-coupling reactions, Stille cross-coupling reactions.

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