Visible-light promoted oxidative cyclization of cinnamic acid derivatives using xanthone as the photocatalyst

2021 ◽  
Author(s):  
Bin Zhao ◽  
Bo Xu
Keyword(s):  
Double Bond ◽  
Visible Light ◽  
Cinnamic Acid ◽  
Oxidative Cyclization ◽  
Coumarin Derivatives ◽  
Cinnamic Acids ◽  
Cinnamic Acid Derivatives ◽  
Double Bond Isomerization ◽  
Photocatalytic Synthesis

We have developed an efficient photocatalytic synthesis of coumarin derivatives via a tandem double bond isomerization/oxidative cyclization of cinnamic acids.

scholarly journals General and Efficient Intermolecular [2+2] Photodimerization of Chalcones and Cinnamic Acid Derivatives in Solution through Visible-Light Catalysis

2017 ◽  
Vol 129 (48) ◽  
pp. 15609-15612 ◽  
Author(s):  
Tao Lei ◽  
Chao Zhou ◽  
Mao-Yong Huang ◽  
Lei-Min Zhao ◽  
Bing Yang ◽  
...  
Keyword(s):  
Visible Light ◽  
Cinnamic Acid ◽  
Cinnamic Acid Derivatives

Microbial Formation of Substituted Styrenes

1989 ◽  
Vol 44 (9-10) ◽  
pp. 765-770 ◽  
Author(s):  
Hans-Adolf Arfmann ◽  
Wolf-Rainer Abraham
Keyword(s):  
Carboxylic Acids ◽  
Benzene Ring ◽  
Cinnamic Acid ◽  
Methoxy Group ◽  
Methyl Chloride ◽  
Side Chains ◽  
Cinnamic Acids ◽  
Cinnamic Acid Derivatives ◽  
Aromatic Carboxylic Acids ◽  
High Yields

Various mono- and disubstituted cinnamic acid derivatives and aromatic carboxylic acids with saturated side chains were incubated mainly with Bacillus, Candida, Hansenula, and Saccharomyces strains. The cinnamic acids carrying a hydroxy- and/or a methoxy group at the 3- and/or 4-position of the benzene ring were decarboxylated with high yields. Most of the reactions were terminated within 24 to 48 h. Substitution at other ring positions afforded also decarboxylation, but at much lower yields. Derivatives with other residues like methyl, chloride, or bromide were not transform ed to the respective styrene. None of the saturated aromatic carboxylic acids could be decarboxylated by the strains used.

scholarly journals Chemo-Enzymatic Cascade for the Generation of Fragrance Aldehydes

Catalysts ◽  
2021 ◽  
Vol 11 (8) ◽  
pp. 932
Author(s):  
Daniel Schwendenwein ◽  
Anna K. Ressmann ◽  
Marcello Entner ◽  
Viktor Savic ◽  
Margit Winkler ◽  
...  
Keyword(s):  
Double Bond ◽  
Carboxylic Acid ◽  
Cinnamic Acid ◽  
Cinnamic Acid Derivatives ◽  
Saccharomyces Pastorianus ◽  
Enzymatic Reduction ◽  
Target Molecules ◽  
Metal Catalyzed ◽  
High Throughput Assay

In this study, we present the synthesis of chiral fragrance aldehydes, which was tackled by a combination of chemo-catalysis and a multi-enzymatic in vivo cascade reaction and the development of a highly versatile high-throughput assay for the enzymatic reduction of carboxylic acids. We investigated a biocompatible metal-catalyzed synthesis for the preparation of α or β substituted cinnamic acid derivatives which were fed directly into the biocatalytic system. Subsequently, the target molecules were synthesized by an enzymatic cascade consisting of a carboxylate reduction, followed by the selective C-C double bond reduction catalyzed by appropriate enoate reductases. We investigated a biocompatible oxidative Heck protocol and combined it with cells expressing a carboxylic acid reductase from Neurospora crassa (NcCAR) and an ene reductase from Saccharomyces pastorianus for the production fragrance aldehydes.

scholarly journals Understanding the role played by protic ionic liquids (PILs) and the substituent effect for enhancing the generation of Z-cinnamic acid derivatives

2020 ◽  
Vol 19 (6) ◽  
pp. 819-830 ◽  
Author(s):  
Rocío B. Rodríguez ◽  
Ramiro L. Zapata ◽  
María L. Salum ◽  
Rosa Erra-Balsells
Keyword(s):  
Ionic Liquids ◽  
Cinnamic Acid ◽  
Substituent Effect ◽  
Pure Acid ◽  
Protic Ionic Liquids ◽  
Cinnamic Acids ◽  
Cinnamic Acid Derivatives

Cinnamic acids in their PIL form are more reactive than in their pure acid forms toward photoisomerization. This knowledge is successfully used for establishing an efficient and practical synthetic protocol for synthesizing Z-cinnamic derivatives.

scholarly journals The efficient and selective catalytic oxidation of para-substituted cinnamic acid derivatives by the cytochrome P450 monooxygenase, CYP199A4

RSC Advances ◽  
2016 ◽  
Vol 6 (60) ◽  
pp. 55286-55297 ◽  
Author(s):  
Rebecca R. Chao ◽  
James J. De Voss ◽  
Stephen G. Bell
Keyword(s):  
Cytochrome P450 ◽  
Catalytic Oxidation ◽  
Cinnamic Acid ◽  
Product Formation ◽  
Cytochrome P450 Enzyme ◽  
Cinnamic Acids ◽  
P450 Monooxygenase ◽  
Cinnamic Acid Derivatives ◽  
Selective Catalytic Oxidation ◽  
P450 Enzyme

The cytochrome P450 enzyme, CYP199A4 oxidised para substituted alkyloxy- and alkyl-cinnamic acids, with high product formation activity.

scholarly journals General and Efficient Intermolecular [2+2] Photodimerization of Chalcones and Cinnamic Acid Derivatives in Solution through Visible-Light Catalysis

2017 ◽  
Vol 56 (48) ◽  
pp. 15407-15410 ◽  
Author(s):  
Tao Lei ◽  
Chao Zhou ◽  
Mao-Yong Huang ◽  
Lei-Min Zhao ◽  
Bing Yang ◽  
...  
Keyword(s):  
Visible Light ◽  
Cinnamic Acid ◽  
Cinnamic Acid Derivatives

Visible-light initiated oxidative cyclization of phenyl propiolates with sulfinic acids to coumarin derivatives under metal-free conditions

2015 ◽  
Vol 51 (35) ◽  
pp. 7520-7523 ◽  
Author(s):  
Wenchao Yang ◽  
Shuai Yang ◽  
Pinhua Li ◽  
Lei Wang
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Oxidative Cyclization ◽  
Coumarin Derivatives ◽  
Metal Free ◽  
Sulfinic Acids

A visible-light initiated oxidative cyclization of phenyl propiolates with sulfinic acids has been developed at room temperature under metal-free conditions.

Visible-Light-Mediated Oxidative Decarboxylative Coupling of Cinnamic Acid Derivatives with Tetrahydrofuran

Synlett ◽  
2015 ◽  
Vol 26 (20) ◽  
pp. 2849-2852 ◽  
Author(s):  
Zheng Liu ◽  
Leifeng Wang ◽  
Dong Liu ◽  
Zhigang Wang
Keyword(s):  
Visible Light ◽  
Cinnamic Acid ◽  
Cinnamic Acid Derivatives ◽  
Decarboxylative Coupling
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