Green Photoorganocatalytic Synthesis of Phenols from Arylboronic Acids

Synlett ◽  
2017 ◽  
Vol 29 (10) ◽  
pp. 1324-1328 ◽  
Author(s):  
Christoforos Kokotos ◽  
Ioanna Sideri ◽  
Errika Voutyritsa
Keyword(s):  
Functional Groups ◽  
Room Temperature ◽  
Boronic Acids ◽  
Light Irradiation ◽  
Reaction Conditions ◽  
Arylboronic Acids ◽  
Water As Solvent ◽  
High Yields

A green and cheap protocol for the photocatalytic hydroxylation of arylboronic acids is presented. 2,2-Dimethoxy-2-phenylacetophenone proved to be the best photoinitiator, among a range of organocatalysts in promoting this reaction. This photocatalytic protocol can be expanded into a wide substrate scope of aromatic boronic acids bearing various functional groups, leading to the corresponding phenols in good to high yields under mild reaction conditions, which include water as solvent, light irradiation provided from standard light-bulbs at room temperature.

Copper-Catalyzed N-Arylation of Sulfoximines with Arylboronic Acids under Mild Conditions

Synthesis ◽  
2019 ◽  
Vol 51 (10) ◽  
pp. 2171-2182 ◽  
Author(s):  
Surabhi Gupta ◽  
Siddharth Baranwal ◽  
Nalluchamy Muniyappan ◽  
Shahulhameed Sabiah ◽  
Jeyakumar Kandasamy
Keyword(s):  
Room Temperature ◽  
Boronic Acids ◽  
Methionine Sulfoximine ◽  
Reaction Conditions ◽  
Biologically Relevant ◽  
Arylboronic Acids ◽  
Mild Conditions ◽  
Short Span ◽  
Sterically Hindered ◽  
First Time

N-Arylation of sulfoximines with different arylboronic acids, including sterically hindered boronic acids, is achieved using copper(I) iodide and 4-DMAP at room temperature. Moreover, N-arylation of biologically relevant l-methionine sulfoximine is demonstrated for the first time. All these reactions provided the desired products in excellent yields within a short span of time. The optimized reaction conditions are well suited to the task of N-vinylation of sulfoximine with trans-2-phenylvinylboronic acid.

A Copper(I)-Mediated Tandem Three-Component Synthesis of 5-Allyl-1,2,3-triazoles

Synthesis ◽  
2019 ◽  
Vol 52 (05) ◽  
pp. 744-754
Author(s):  
Yoona Song ◽  
Soyun Lee ◽  
Palash Dutta ◽  
Jae-Sang Ryu
Keyword(s):  
Room Temperature ◽  
Reaction Conditions ◽  
One Pot ◽  
Three Component Reaction ◽  
High Yields

A copper(I)-mediated tandem three-component reaction using alkynes, azides, allyl iodides, CuI and NaNH2 is developed. The reactions proceed smoothly at room temperature to afford 5-allyl-1,2,3-triazoles, which can be further converted into 1,2,3-triazole-fused tricyclic scaffolds. This method features an efficient one-pot cascade route using commercial alkynes and affords the corresponding 5-allyl-1,2,3-triazoles with high yields and good selectivity under mild reaction conditions.

Room temperature nickel-catalyzed cross-coupling of aryl-boronic acids with thiophenols: synthesis of diarylsulfides

2020 ◽  
Vol 18 (13) ◽  
pp. 2447-2458 ◽  
Author(s):  
Amit Bhowmik ◽  
Mahesh Yadav ◽  
Rodney A. Fernandes
Keyword(s):  
Room Temperature ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Arylboronic Acids

A mild and easy to operate NiCl2/2,2′-bipyridine-catalyzed cross-coupling of thiophenols with arylboronic acids has been developed for the synthesis of symmetric and unsymmetric diarylsulfides at room temperature and in air.

scholarly journals Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction

2019 ◽  
Vol 15 ◽  
pp. 874-880
Author(s):  
Razieh Navari ◽  
Saeed Balalaie ◽  
Saber Mehrparvar ◽  
Fatemeh Darvish ◽  
Frank Rominger ◽  
...  
Keyword(s):  
Room Temperature ◽  
High Selectivity ◽  
Domino Reaction ◽  
Primary Amines ◽  
Efficient Synthesis ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Efficient Approach ◽  
Three Component Reaction ◽  
High Yields

An efficient approach for the synthesis of pyrazolopyridines containing the aminochromane motif through a base-catalyzed cyclization reaction is reported. The synthesis was carried out through a three-component reaction of (arylhydrazono)methyl-4H-chromen-4-one, malononitrile, primary amines in the presence of Et3N at room temperature. However, carrying out the reaction under the same conditions without base led to a fused chromanyl-cyanopyridine. High selectivity, high atom economy, and good to high yields in addition to mild reaction conditions are the advantages of this approach.

Water-Assisted Organocatalysis: An Enantioselective Green Protocol for the Henry Reaction

2013 ◽  
Vol 66 (6) ◽  
pp. 661 ◽  
Author(s):  
Prashant B. Thorat ◽  
Santosh V. Goswami ◽  
Wamanrao N. Jadhav ◽  
Sudhakar R. Bhusare
Keyword(s):  
Hydrogen Bonding ◽  
Room Temperature ◽  
Enantioselective Synthesis ◽  
Henry Reaction ◽  
Reaction Conditions ◽  
Green Protocol ◽  
Excellent Yield ◽  
Water As Solvent ◽  
Nitroaldol Reaction ◽  
Work Up

We report an enantioselective Henry (nitroaldol) reaction catalysed by an organocatalyst using water as solvent. The enantioselective synthesis of β-nitroalcohols was achieved by using a neutral chiral organocatalyst, through strong hydrogen bonding, which results in the formation of corresponding products in excellent yield and enantioselectivity at room temperature. Other attractive features of the method are the eco-friendly, non-hazardous, and mild reaction conditions, inexpensive catalyst, and simple work up conditions.

Metal free visible light driven oxidation of alcohols to carbonyl derivatives using 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) as catalyst

RSC Advances ◽  
2015 ◽  
Vol 5 (102) ◽  
pp. 84328-84333 ◽  
Author(s):  
Suvendu Samanta ◽  
Papu Biswas
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Light Irradiation ◽  
Metal Free ◽  
Carbonyl Derivatives ◽  
Oxidation Of Alcohols ◽  
Visible Light Driven ◽  
High Yields

A metal-free transformation of alcohols to the corresponding carbonyls in high yields under visible-light irradiation has been achieved at room temperature using di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) as catalyst.

scholarly journals Sulfoximines-Assisted Rh(III)-Catalyzed C–H Activation and Intramolecular Annulation for the Synthesis of Fused Isochromeno-1,2-Benzothiazines Scaffolds under Room Temperature

Molecules ◽  
2020 ◽  
Vol 25 (11) ◽  
pp. 2515
Author(s):  
Bao Wang ◽  
Xu Han ◽  
Jian Li ◽  
Chunpu Li ◽  
Hong Liu
Keyword(s):  
Functional Groups ◽  
Room Temperature ◽  
Reaction Conditions

A mild and facile Cp*Rh(III)-catalyzed C–H activation and intramolecular cascade annulation protocol has been proposed for the furnishing of highly fused isochromeno-1,2-benzothiazines scaffolds using S-phenylsulfoximides and 4-diazoisochroman-3-imine as substrates under room temperature. This method features diverse substituents and functional groups tolerance and relatively mild reaction conditions with moderate to excellent yields. Additionally, retentive configuration of sulfoximides in the conversion has been verified.

Room Temperature Coupling of Aryldiazoacetates with Boronic Acids Enhanced by Blue Light Irradiation

2020 ◽  
Vol 26 (25) ◽  
pp. 5648-5653 ◽  
Author(s):  
Amanda F. Silva ◽  
Marco A. S. Afonso ◽  
Rodrigo A. Cormanich ◽  
Igor D. Jurberg
Keyword(s):  
Blue Light ◽  
Room Temperature ◽  
Boronic Acids ◽  
Light Irradiation

scholarly journals An Efficient Protocol for the Synthesis of Quinoxaline Derivatives at Room Temperature Using Recyclable Alumina-Supported Heteropolyoxometalates

2012 ◽  
Vol 2012 ◽  
pp. 1-8 ◽  
Author(s):  
Diego M. Ruiz ◽  
Juan C. Autino ◽  
Nancy Quaranta ◽  
Patricia G. Vázquez ◽  
Gustavo P. Romanelli
Keyword(s):  
Room Temperature ◽  
Incipient Wetness Impregnation ◽  
Reaction Conditions ◽  
Commercial Alumina ◽  
Mild Conditions ◽  
Quinoxaline Derivatives ◽  
Incipient Wetness ◽  
High Yields ◽  
Catalytic Test

We report a suitable quinoxaline synthesis using molybdophosphovanadates supported on commercial alumina cylinders as catalysts. These catalysts were prepared by incipient wetness impregnation. The catalytic test was performed under different reaction conditions in order to know the performance of the synthesized catalysts. The method shows high yields of quinoxaline derivatives under heterogeneous conditions. Quinoxaline formation was obtained using benzyl,o-phenylenediamine, and toluene as reaction solvent at room temperature. The CuH2PMo11VO40supported on alumina showed higher activity in the tested reaction. Finally, various quinoxalines were prepared under mild conditions and with excellent yields.

Synthesis, characterization of active Sn(0), and its application in selective propargylation of aldehyde at room temperature in water

2019 ◽  
Vol 97 (1) ◽  
pp. 29-36 ◽  
Author(s):  
Paresh Nath Chatterjee ◽  
Dipankar Paul ◽  
Micky Lanster Sawkmie ◽  
Arun Kumar Sinha ◽  
Snehadrinarayan Khatua
Keyword(s):  
Carboxylic Acid ◽  
Functional Groups ◽  
Room Temperature ◽  
Chemical Reduction ◽  
Inert Atmosphere ◽  
Reducing Agent ◽  
Distilled Water ◽  
Propargyl Bromide ◽  
High Yields

Active Sn(0) particles are synthesized in high yields by the chemical reduction of the blue–black stannous oxide using freshly prepared sodium stannite solution as reducing agent at 40 °C and 60 °C. The Sn(0) particles are characterized using powder XRD, SEM, and DSC. The as-synthesized Sn(0) particles are applied as reagent for the regioselective synthesis of homopropargyl alcohols from propargyl bromide and aldehydes in distilled water at room temperature (in 50%–84% yields). No assistance of heat, microwave, ultrasound, organic co-solvent, co-reagent, or inert atmosphere is required for this reaction. The propargylation reaction is highly chemoselective towards aldehyde over other less electrophilic carbonyl functional groups such as ketone, amide, and carboxylic acid. Our in-house synthesized homopropargyl alcohols can be used to synthesize conjugated 1,3-diynes.

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