192573-53-8

Upstream product

• 201230-82-2 carbon monoxide 
• 768-70-7 1-ethynyl-3-methoxybenzene 
• 62-53-3 aniline 
• 1864-94-4 phenyl formate 
• 611-73-4 Benzoylformic acid 
• 591-50-4 iodobenzene 
• 100-52-7 benzaldehyde 
• 40230-92-0 3-(trimethylsilylethynyl)anisole 
• 766-85-8 3-methoxy-1-iodobenzene 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 6125-26-4 phenyl(2-phenyl-2,3-dihydrobenzo[d]thiazol-2-yl)methanone 
• 134-81-6 benzil 
• 124-38-9 carbon dioxide 
• 98-88-4 benzoyl chloride 

Downstream Products

• 1202553-44-3 (R)-3-benzyl-7-(3-methoxy-phenyl)-5-phenyl-2,3-dihydro-1,4-oxazepine 
• 1202553-45-4 (S)-3-((S)-sec-butyl)-7-(3-methoxy-phenyl)-5-phenyl-2,3-dihydro-1,4-oxazepine 
• 1202553-61-4 (Z)-3-(3H-inden-1-ylamino)-1-(3-methoxy-phenyl)-3-phenyl-prop-2-enone 
• 1202553-58-9 6-(3-methoxy-phenyl)-2-methyl-2,4-diphenyl-2H-1,3-oxazine 
• 25856-11-5 5-(3-methoxy-phenyl)-3-phenyl-isoxazole 
• 404377-69-1 2-(3-methoxyphenyl)-5-methyl-1,3-benzoxazole 

Relevant academic research and scientific papers

Synthesis of Fluorescent 1,3-Diarylpropynones by Carbonylative Alkynylation Reaction Using (Phosphine) (1,2,3-triazol-5-ylidene)palladium Complexes as Catalysts

The synthesis of a variety of 1,3-diarylpropynones that contain not only substituted phenyl groups but also fluorophoric 1-pyrenyl, 3-carbazolyl, and 1-naphthyl groups was achieved in good to excellent yields by using a carbonylative alkynylation reaction in the presence of cis-(Tz)Pd(Cl)2(PPh3) (Tz = 1,2,3-triazol-5-ylidene) as a precatalyst under 1.0 atm of CO. Products resulting from competing Sonogashira coupling reactions, namely 1,2-diarylacetylenes, were not observed. The synthesized ynones exhibit fluorescence not only in solution but also in the solid state. The catalytically active palladium species was recovered and reused for up to three cycles by adsorbing the cis-(Tz)Pd(Cl)2(PPh3) precatalyst onto silica gel and carrying out the reaction under heterogeneous conditions.

One-Pot Palladium-Catalyzed Carbonylative Sonogashira Coupling using Carbon Dioxide as Carbonyl Source

Carbonylation coupling reaction has emerged as a powerful and versatile strategy for the construction of carbonyl-containing compounds in modern synthetic chemistry over the past years. Carbon dioxide, a renewable one carbon molecule, has become one of the most attractive and promising alternative carbonyl sources due to its highly abundance, nontoxicity and stability in comparison with CO in recent years. However, in most cases, a two-chamber technique was generally necessary to allow the CO-producing and CO-consuming processes to perform successfully because of the complexities and incompatibility of reaction conditions, when carbon dioxide was utilized as carbonyl source. Herein, a practical one-pot protocol using carbon dioxide as the carbonyl source for the palladium-catalyzed carbonylative Sonogashira coupling has been established, providing an expedient and practical route to a wide range of functionalized alkynones and indoxyls under mild reaction conditions. By finding a suitable catalytic system, the method allowed the CO-generating and CO-consuming processes to proceed in one pot, wherein carbon monoxide was generated in situ from the reduction of carbon dioxide in the absence of any fluoride reagents. Simple and safe operation, readily available substrates, good functional group tolerance and mild reaction conditions are the features of the method.

Base-Promoted Synthesis of Polysubstituted 4-Aminoquinolines from Ynones and 2-Aminobenzonitriles under Transition-Metal-Free Conditions

A transition-metal-free and base-promoted one-pot reaction of ynones with 2-aminobenzonitriles is described. The reaction was initiated through sequential aza-Michael addition/intramolecular annulation to afford various multisubstituted 4-aminoquinolines

Acyl Radicals from Benzothiazolines: Synthons for Alkylation, Alkenylation, and Alkynylation Reactions

We describe herein a fundamentally new visible light-driven homolytic C-C bond breaking mode for the generation of acyl radicals from C2-acyl-substituted benzothiazolines. The reactive species can be used as versatile synthons for formal radical alkylatio

Synthesis of benzoxazoles via the copper-catalyzed hydroamination of alkynones with 2-aminophenols

We describe herein the synthetic method to benzoxazole derivatives via the copper-catalyzed hydroamination of alkynones with 2-aminophenols. The method produced a wide variety of functionalized benzoxazole derivatives in good yields. Preliminary mechanistic experiments revealed that the reaction would proceed through the copper-catalyzed hydroamination of alkynones and the sequential intramolecular cyclization of β-iminoketones/elimination of acetophenone promoted by the copper catalyst.

Copper-Mediated Domino Cyclization/Trifluoromethylation/Deprotection with TMSCF3: Synthesis of 4-(Trifluoromethyl)pyrazoles

A copper-mediated synthesis of 4-(trifluoromethyl)pyrazoles is described. In one step from readily accessible α,β-alkynic tosylhydrazones, a remarkable domino sequence of cyclization, trifluoromethylation, and detosylation takes place to furnish the 4-CF3 N-H pyrazole cores with good functional group compatibility. The reaction conditions are mild and convenient, at room temperature in air, using the commercially available trifluoromethyltrimethylsilane (TMSCF3) as the CF3 source. The method can be applied to the synthesis of a 4-CF3 analogue of the anti-inflammatory drug celecoxib.

Alkynylation of Csp2 (O)–H Bonds Enabled by Photoredox-Mediated Hydrogen-Atom Transfer

The development of new hydrogen-atom transfer (HAT) strategies within the framework of photoredox catalysis is highly appealing for its power to activate a desired C?H bond in the substrate leading to its selective functionalization. Reported here is the first photoredox-mediated hydrogen-atom transfer method for the efficient synthesis of ynones, ynamides, and ynoates with high regio- and chemoselectivity by direct functionalization of Csp2 (O)?H bonds. The broad synthetic application of this method has been demonstrated by the selective functionalization of C(O)?H bonds within complex molecular scaffolds.

Dual Hypervalent Iodine(III) Reagents and Photoredox Catalysis Enable Decarboxylative Ynonylation under Mild Conditions

A combination of hypervalent iodine(III) reagents (HIR) and photoredox catalysis with visible light has enabled chemoselective decarboxylative ynonylation to construct ynones, ynamides, and ynoates. This ynonylation occurs effectively under mild reaction conditions at room temperature and on substrates with various sensitive and reactive functional groups. The reaction represents the first HIR/photoredox dual catalysis to form acyl radicals from α-ketoacids, followed by an unprecedented acyl radical addition to HIR-bound alkynes. Its efficient construction of an mGlu5 receptor inhibitor under neutral aqueous conditions suggests future visible-light-induced biological applications.

Transition-Metal-Free Synthesis of Ynones via Decarboxylative Alkynylation of α-Keto Acids under Mild Conditions

A transition-metal-free synthetic method of various ynones via decarboxylative alkynylation of α-keto acids is described. The reaction is carried out under mild conditions and exhibits remarkable tolerance of functional groups. The mechanism of a radical

Aryl formate as bifunctional reagent: Applications in palladium-catalyzed carbonylative coupling reactions using in situ generated CO

After decades of development, carbonylation reactions have become one of the most powerful tools in modern organic synthesis. However, the requirement of CO gas limits the applications of such reactions. Reported herein is a versatile and practical protocol for carbonylative reactions which rely on the cooperation of phenyl formate and nonaflate, and the generation of CO in situ. This protocol has a high functional-group tolerance and could be applied in carbonylations with C, N, and, O nucleophiles. The corresponding amides, alkynones, furanones, and aryl benzoates were synthesized in good yields. Transformers: A versatile and practical protocol for carbonylation reactions involve the cooperation of phenyl formate and nonaflate with generation of CO in situ. This protocol has a high functional-group tolerance and could be applied in carbonylative couplings with C, N, and O nucleophiles. The corresponding amides, alkynones, furanones, and aryl benzoates were synthesized in good yield.