BODIPY catalyzed amide synthesis promoted by BHT and air under visible light

2016 ◽  
Vol 14 (29) ◽  
pp. 7028-7037 ◽  
Author(s):  
Xiao-Fei Wang ◽  
Shu-Sheng Yu ◽  
Chao Wang ◽  
Dong Xue ◽  
Jianliang Xiao
Keyword(s):  
Visible Light ◽  
Aromatic Aldehydes ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Amide Synthesis ◽  
Oxidative Amidation

A novel and efficient protocol for the synthesis of amides is reported via a BODIPY catalyzed oxidative amidation of aromatic aldehydes under visible light, with broad substrate scope and mild reaction conditions. Mechanistic studies reveal that dioxygen could be activated through both an ET and SET pathway to form the active peroxide intermediates.

ChemInform Abstract: Visible-Light-Mediated Decarboxylation/Oxidative Amidation of α-Keto Acids with Amines under Mild Reaction Conditions Using O2.

ChemInform ◽  
2014 ◽  
Vol 45 (30) ◽  
pp. no-no
Author(s):  
Jie Liu ◽  
Qiang Liu ◽  
Hong Yi ◽  
Chu Qin ◽  
Ruopeng Bai ◽  
...  
Keyword(s):  
Visible Light ◽  
Reaction Conditions ◽  
Keto Acids ◽  
Oxidative Amidation

scholarly journals Visible-Light, Iodine-Promoted Formation of N-Sulfonyl Imines and N-Alkylsulfonamides from Aldehydes and Hypervalent Iodine Reagents

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 1838 ◽  
Author(s):  
Megan Hopkins ◽  
Zachary Brandeburg ◽  
Andrew Hanson ◽  
Angus Lamar
Keyword(s):  
Drug Discovery ◽  
Visible Light ◽  
Initial Step ◽  
Hypervalent Iodine ◽  
Mechanistic Studies ◽  
Synthetic Methodology ◽  
Reaction Conditions ◽  
Drug Discovery And Development ◽  
Radical Initiator ◽  
Reaction Proceeds

Alternative synthetic methodology for the direct installation of sulfonamide functionality is a highly desirable goal within the domain of drug discovery and development. The formation of synthetically valuable N-sulfonyl imines from a range of aldehydes, sulfonamides, and PhI(OAc)2 under practical and mild reaction conditions has been developed. According to mechanistic studies described within, the reaction proceeds through an initial step involving a radical initiator (generated either by visible-light or heat) to activate the reacting substrates. The reaction provides a synthetically useful and operationally simple, relatively mild alternative to the traditional formation of N-sulfonyl imines that utilizes stable, widely available reagents.

scholarly journals Exploring organic photosensitizers based on hemicyanine derivatives: a sustainable approach for preparation of amide linkages

RSC Advances ◽  
2018 ◽  
Vol 8 (54) ◽  
pp. 31237-31245 ◽  
Author(s):  
Harnimarta Deol ◽  
Manoj Kumar ◽  
Vandana Bhalla
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Aqueous Media ◽  
Aromatic Aldehydes ◽  
Light Irradiation ◽  
Oxidative Amidation

Hemicyanine derivatives C1–C4 have been synthesized and utilized as photocatalysts in additive/base free oxidative amidation of aromatic aldehydes in mixed aqueous media under visible light irradiation at low catalytic loading.

Synthesis of Ag/g-C3 N4 Composite as Highly Efficient Visible-Light Photocatalyst for Oxidative Amidation of Aromatic Aldehydes

2016 ◽  
Vol 358 (16) ◽  
pp. 2631-2641 ◽  
Author(s):  
Lingling Wang ◽  
Min Yu ◽  
Chaolong Wu ◽  
Nan Deng ◽  
Chao Wang ◽  
...  
Keyword(s):  
Visible Light ◽  
Aromatic Aldehydes ◽  
Visible Light Photocatalyst ◽  
Highly Efficient ◽  
Oxidative Amidation

Visible-Light-Mediated Decarboxylation/Oxidative Amidation of α-Keto Acids with Amines under Mild Reaction Conditions Using O2

2013 ◽  
Vol 53 (2) ◽  
pp. 502-506 ◽  
Author(s):  
Jie Liu ◽  
Qiang Liu ◽  
Hong Yi ◽  
Chu Qin ◽  
Ruopeng Bai ◽  
...  
Keyword(s):  
Visible Light ◽  
Reaction Conditions ◽  
Keto Acids ◽  
Oxidative Amidation

Visible-Light-Mediated Decarboxylation/Oxidative Amidation of α-Keto Acids with Amines under Mild Reaction Conditions Using O2

2013 ◽  
Vol 126 (2) ◽  
pp. 512-516 ◽  
Author(s):  
Jie Liu ◽  
Qiang Liu ◽  
Hong Yi ◽  
Chu Qin ◽  
Ruopeng Bai ◽  
...  
Keyword(s):  
Visible Light ◽  
Reaction Conditions ◽  
Keto Acids ◽  
Oxidative Amidation

DFT Study and Synthesis of Novel Bioactive Bispyrazole Using Mg/AlLDH as a Solid Base Catalyst

2020 ◽  
Vol 14 ◽  
Author(s):  
Soufiane Akhramez ◽  
Youness Achour ◽  
Mustapha Diba ◽  
Lahoucine Bahsis ◽  
Hajiba Ouchetto ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Experimental Finding ◽  
Biological Activities ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
Mechanistic Study ◽  
Knoevenagel Reaction ◽  
Solid Base ◽  
Reaction Conditions ◽  
Aryl Aldehyde

Background: In this study, an efficient synthesis of novel bispyrazole heterocyclic molecules by condensation of substituted aromatic aldehydes with 1,3-diketo-N-phenylpyrazole by using Mg/Al-LDH as heterogeneous catalyst is reported. The attractive features of this protocol are as follows: mild reaction conditions, good yields and easiness of the catalyst separation from the reaction mixture. Further, a mechanistic study has been performed by using DFT calculations to explain the observed selectivity of the condensation reaction between aryl aldehyde and 1,3-diketo-N-phenylpyrazole via Knoevenagel reaction. The local electrophilicity/ nucleophilicity that allows explaining correctly the experimental finding. Methods: The bispyrazole derivatives 3a-m were prepared by condensation reaction of substituted aromatic aldehydes with 1,3-diketo-Nphenylpyrazole by using Mg/Al-LDH as heterogeneous catalyst under THF solvent at the refluxing temperature. Objective: To synthesize a novel bispyrazole heterocyclic molecule may be have important biological activities and thus can be good candidates for pharmaceutical applications. Results: This protocol describes the Synthesis of Bioactive Compounds under mild reaction conditions, good yields and easiness of the catalyst separation from the reaction mixture. Further, a mechanistic study has been performed by using DFT calculations to explain the observed selectivity of the condensation reaction between aryl aldehyde and 1,3-diketo-N-phenylpyrazole via Knoevenagel reaction. The local electrophilicity/ nucleophilicity that allows explaining correctly the experimental finding. Conclusion: In summary, the pharmacologically interesting bis-pyrazole derivatives have been synthesized through Mg/Al-LDH as a solid base catalyst, in THF as solvent. Thus, the synthesized bioactive compounds containing the pyrazole ring may be have important biological activities and thus can be good candidates for pharmaceutical applications. Therefore, the catalyst Mg/Al-LDH showed high catalytic activity. Besides, a series of bispyrazole molecules were synthesized with a good yield and easy separation of the catalyst by simple filtration. Moreover, DFT calculations and reactivity indexes are used to explain the selectivity of the condensation reaction between aryl benzaldehyde and 1,3-diketo-Nphenylpyrazole via Knoevenagel reaction, and the results are in good agreement with the experimental finding.

Visible-Light-Initiated Manganese Catalysis for C−H Alkylation of Heteroarenes: Applications and Mechanistic Studies

2017 ◽  
Vol 56 (48) ◽  
pp. 15309-15313 ◽  
Author(s):  
Philippe Nuhant ◽  
Martins S. Oderinde ◽  
Julien Genovino ◽  
Antoine Juneau ◽  
Yohann Gagné ◽  
...  
Keyword(s):  
Visible Light ◽  
Mechanistic Studies

Fluorinated Solvent-Assisted Photocatalytic Aerobic Oxidative Amidation of Alcohols via Visible-Light-Mediated ‎ HKUST-1/Cs-POMoW Catalysis.

2021 ◽  
Author(s):  
Meghdad Karimi ◽  
Samira Sadeghi ◽  
Haleh Mohebali ◽  
Zahra Azarkhosh ◽  
Vahid Safarifard ◽  
...  
Keyword(s):  
Visible Light ◽  
Metal Organic Frameworks ◽  
Metal Organic ◽  
Oxidative Amidation

Considering the irreplaceable importance of photocatalytic functionalization reactions and the widespread attention paid to the use of metal-organic frameworks, especially their modified variants for this purpose in recent years, different...

A review of lignin hydrogen peroxide oxidation chemistry with emphasis on aromatic aldehydes and acids

Holzforschung ◽  
2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Ajinkya More ◽  
Thomas Elder ◽  
Zhihua Jiang
Keyword(s):  
Hydrogen Peroxide ◽  
Oxidative Degradation ◽  
Reaction Medium ◽  
Dicarboxylic Acids ◽  
Aromatic Aldehydes ◽  
Product Distribution ◽  
Reaction Conditions ◽  
Alkaline Conditions ◽  
The Stability ◽  
Oxidation Chemistry

Abstract This review discusses the main factors that govern the oxidation processes of lignins into aromatic aldehydes and acids using hydrogen peroxide. Aromatic aldehydes and acids are produced in the oxidative degradation of lignin whereas mono and dicarboxylic acids are the main products. The stability of hydrogen peroxide under the reaction conditions is an important factor that needs to be addressed for selectively improving the yield of aromatic aldehydes. Hydrogen peroxide in the presence of heavy metal ions readily decomposes, leading to minor degradation of lignin. This degradation results in quinones which are highly reactive towards peroxide. Under these reaction conditions, the pH of the reaction medium defines the reaction mechanism and the product distribution. Under acidic conditions, hydrogen peroxide reacts electrophilically with electron rich aromatic and olefinic structures at comparatively higher temperatures. In contrast, under alkaline conditions it reacts nucleophilically with electron deficient carbonyl and conjugated carbonyl structures in lignin. The reaction pattern in the oxidation of lignin usually involves cleavage of the aromatic ring, the aliphatic side chain or other linkages which will be discussed in this review.

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