Copper-catalysed cross-coupling affected by the Smiles rearrangement: a new chapter on diversifying the synthesis of chiral fluorinated 1,4-benzoxazine derivatives

RSC Advances ◽  
2015 ◽  
Vol 5 (102) ◽  
pp. 83576-83580 ◽  
Author(s):  
Saba Alapour ◽  
Deresh Ramjugernath ◽  
Neil A. Koorbanally
Keyword(s):  
Room Temperature ◽  
Cross Coupling ◽  
Smiles Rearrangement ◽  
Derivatives Of

Synthesis of novel derivatives of fluorinated benzoxazines was achieved through the Smiles rearrangement. The gauche conformation of selected precursors enabled the reaction to occur at room temperature at yields of 90%.

scholarly journals N-Directed Pd-Catalyzed Photoredox-Mediated C–H Arylation for Accessing Phenyl-Extended Analogues of Biginelli/Suzuki-Derived Ethyl 4-Methyl-2,6-diphenylpyrimidine-5-carboxylates

Catalysts ◽  
2021 ◽  
Vol 11 (9) ◽  
pp. 1071
Author(s):  
Savvas N. Georgiades ◽  
Persefoni G. Nicolaou ◽  
Nikos Panagiotou
Keyword(s):  
Organic Synthesis ◽  
Phenyl Ring ◽  
Room Temperature ◽  
Functional Group ◽  
Cross Coupling ◽  
Steric Effects ◽  
Biologically Relevant ◽  
Biginelli Condensation ◽  
Derivatives Of ◽  
Electronic And Steric Effects

The availability and application of direct, functional group-compatible C–H activation methods for late-stage modification of small-molecule bioactives and other valuable materials remains an ongoing challenge in organic synthesis. In the current study, we demonstrate that a LED-activated, photoredox-mediated, Pd(OAc)2-catalyzed C–H arylation, employing a phenyldiazonium aryl source and either tris(2,2′-bipyridine)ruthenium(II) or (2,2′-bipyridine)bis[3,5-di-fluoro-2-[5-(trifluoromethyl)-2-pyridinyl-kN][phenyl-kC]iridium(III) as photoredox initiator, may successfully produce unprecedented mono- and bis-phenyl derivatives of functionality-rich 2,6-diphenylpyrimidine substrates at room temperature. The series of 19 substrates employed herein, which share the biologically-relevant 4-methyl-2,6-diphenylpyrimidine-5-carboxylate scaffold, were generated via a synthetic route involving (3-component) Biginelli condensation, oxidative dehydrogenation of the obtained 3,4-dihydropyrimidin-2(1H)-one to 2-hydroxypyrimidine, O-sulfonylation, and Suzuki-Miyaura C–C cross-coupling. Submission of these substrates to pyrimidine-N-atom-directed C–H arylation conditions led to regioselective phenylation at the ortho site(s) of the pyrimidine-C2-connected phenyl ring, revealing substituent-dependent electronic and steric effects. A focused library of 18 mono- and 10 bis-phenyl derivatives was generated. Its members exhibit interesting 3D and peripheral substitution features that render them promising for evaluation in drug discovery efforts.

Development of the room temperature protocol based on room temperature ionic liquids and surfactant ionic liquids for the synthesis of derivatives of 2-amino-thiazoles and thermo-physical analysis of the synthesized derivatives using TGA-DSC.

2020 ◽  
Vol 10 ◽  
Author(s):  
Chandrakant Sarode ◽  
Sachin Yeole ◽  
Ganesh Chaudhari ◽  
Govinda Waghulde ◽  
Gaurav Gupta
Keyword(s):  
Thermal Analysis ◽  
Heat Capacity ◽  
Ionic Liquids ◽  
Specific Heat ◽  
Specific Heat Capacity ◽  
Room Temperature ◽  
Heat Capacity Data ◽  
General Strategy ◽  
Capacity Data ◽  
Derivatives Of

Aims: To develop an efficient protocol, which involves an elegant exploration of the catalytic potential of both the room temperature and surfactant ionic liquids towards the synthesis of biologically important derivatives of 2-aminothiazole. Objective: Specific heat capacity data as a function of temperature for the synthesized 2- aminothiazole derivatives has been advanced by exploring their thermal profiles. Method: The thermal gravimetry analysis and differential scanning calorimetry techniques are used systematically. Results: The present strategy could prove to be a useful general strategy for researchers working in the field of surfactants and surfactant based ionic liquids towards their exploration in organic synthesis. In addition to that, effect of electronic parameters on the melting temperature of the corresponding 2-aminothiazole has been demonstrated with the help of thermal analysis. Specific heat capacity data as a function of temperature for the synthesized 2-aminothiazole derivatives has also been reported. Conclusion: Melting behavior of the synthesized 2-aminothiazole derivatives is to be described on the basis of electronic effects with the help of thermal analysis. Additionally, the specific heat capacity data can be helpful to the chemists, those are engaged in chemical modelling as well as docking studies. Furthermore, the data also helps to determine valuable thermodynamic parameters such as entropy and enthalpy.

The Merger of CF3SO2Na and Palladium Catalysis to Enable Decarboxylative Cross-Coupling for the Synthesis of Aromatic Ketones under Room Temperature

2021 ◽  
Author(s):  
Pan Xie ◽  
Cheng Xue ◽  
Cancan Wang ◽  
Dongdong Du ◽  
Sanshan Shi
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Palladium Catalysis ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Aromatic Ketones ◽  
Aryl Ketones ◽  
Oxocarboxylic Acids

A CF3SO2Na/Pd(OAc)2 co-catalyzed strategy is developed to produce aryl ketones via visible-light-induced decarboxylative cross-coupling of α-oxocarboxylic acids and aryl boronic acids. This process was perfomed under air at room temperature,...

Room-Temperature, Water-Promoted, Radical-Coupling Reactions of Phenols with tert-Butyl Nitrite

Synlett ◽  
2017 ◽  
Vol 28 (16) ◽  
pp. 2153-2156 ◽  
Author(s):  
Wen-Ting Wei ◽  
Hongze Liang ◽  
Wen-Ming Zhu ◽  
Weida Liang ◽  
Yi Wu ◽  
...  
Keyword(s):  
Room Temperature ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phenol Derivative ◽  
Tert Butyl ◽  
Radical Coupling ◽  
Air Atmosphere ◽  
Cross Coupling Reaction ◽  
Temperature Water

A radical–radical cross-coupling reaction of phenols with tert-butyl nitrite has been developed with the use of water as an additive. This method allows the construction of C–N bonds under an air atmosphere at room temperature, providing the ortho-nitrated phenol derivative in moderate to good yields.

Palladium-catalyzed Mizoroki–Heck-type reactions of [Ph2SRfn][OTf] with alkenes at room temperature

2016 ◽  
Vol 52 (80) ◽  
pp. 11893-11896 ◽  
Author(s):  
Shi-Meng Wang ◽  
Hai-Xia Song ◽  
Xiao-Yan Wang ◽  
Nan Liu ◽  
Hua-Li Qin ◽  
...  
Keyword(s):  
Room Temperature ◽  
Cross Coupling ◽  
Palladium Catalyzed

The first Pd-catalyzed Mizoroki–Heck-type cross-coupling of phenylsulfonium salts with alkenes was disclosed at room temperature.

ChemInform Abstract: Cross-Coupling of Alkyl Halides with Heteroaromatic Halides, in Water at Room Temperature.

ChemInform ◽  
2011 ◽  
Vol 42 (30) ◽  
pp. no-no
Author(s):  
Arkady Krasovskiy ◽  
Isabelle Thome ◽  
Julien Graff ◽  
Valeria Krasovskaya ◽  
Paul Konopelski ◽  
...  
Keyword(s):  
Room Temperature ◽  
Cross Coupling ◽  
Alkyl Halides
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