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

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...

scholarly journals Copper’s rapid ascent in visible-light photoredox catalysis

Science ◽  
2019 ◽  
Vol 364 (6439) ◽  
pp. eaav9713 ◽  
Author(s):  
Asik Hossain ◽  
Aditya Bhattacharyya ◽  
Oliver Reiser
Keyword(s):  
Visible Light ◽  
Organic Dyes ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Photoredox Catalysis ◽  
Cross Coupling Reactions ◽  
Rapid Ascent ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Visible-light photoredox catalysis offers a distinct activation mode complementary to thermal transition metal catalyzed reactions. The vast majority of photoredox processes capitalizes on precious metal ruthenium(II) or iridium(III) complexes that serve as single-electron reductants or oxidants in their photoexcited states. As a low-cost alternative, organic dyes are also frequently used but in general suffer from lower photostability. Copper-based photocatalysts are rapidly emerging, offering not only economic and ecological advantages but also otherwise inaccessible inner-sphere mechanisms, which have been successfully applied to challenging transformations. Moreover, the combination of conventional photocatalysts with copper(I) or copper(II) salts has emerged as an efficient dual catalytic system for cross-coupling reactions.

7,10-Dibromo-2,3-dicyanopyrazinophenanthrene Aggregates as a Photosensitizer for Nickel-Catalyzed Aryl Esterification

Synlett ◽  
2021 ◽  
Author(s):  
Xiaoqiang Yu ◽  
Min He ◽  
Shilei Yang ◽  
Ming Bao
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Bond Formation ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Ni Catalyst ◽  
Coupling Reactions ◽  
Formation Reaction ◽  
Cross Coupling Reactions ◽  
Reaction Proceeds

AbstractSelf-assembled aggregates of 7,10-dibromo-2,3-dicyanopyrazinophenanthrene which act as a new organophotocatalyst in combination with Ni catalyst for the Caryl–Oacyl cross-coupling reactions of carboxylic acids with aryl halides are described. This visible-light-induced Caryl–Oacyl bond-formation reaction proceeds smoothly to afford aryl esters with satisfactory to excellent yields.

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.

Synthetic studies of novel ninhydrin analogs

2001 ◽  
Vol 79 (11) ◽  
pp. 1632-1654 ◽  
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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