65418-71-5

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 100-07-2 4-methoxy-benzoyl chloride 
• 768-60-5 4-methoxyphenylacetylen 
• 1172584-15-4 1,3-bis(4-methoxyphenyl)prop-2-yn-1-ol 
• 201230-82-2 carbon monoxide 
• 696-62-8 para-iodoanisole 
• 471-25-0 Propiolic acid 
• 132353-25-4 2-(4-methoxybenzoyloxy)-4,6-dimethoxy-1,3,5-triazine 
• 100-09-4 4-methoxybenzoic acid 
• 540-38-5 p-Iodophenol 
• 105-13-5 4-Methoxybenzyl alcohol 
• 4301-14-8 acetylenemagnesium bromide 
• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 

Downstream Products

• 215813-35-7 2-[2-(4-methoxyphenyl)-1,3-dithiolan-2-yl]-1-(4-methoxyphenyl)ethanone 
• 1172584-20-1 4,6-bis-(4-methoxyphenyl)-3-phenyl-pyran-2-one 
• 688743-27-3 2-phenyl-4,6-bis(4-methoxyphenyl)pyrimidine 
• 1436417-39-8 C₃₁H₂₇NO₅ 
• 849024-40-4 3-(4-methoxybenzoyl)-4-(4-methoxyphenyl)furan-2(5H)-one 
• 75059-30-2 3,5-bis(4-methoxiphenyl)-1H-pyrazole 
• 1187957-99-8 1,3-bis(4-hydroxyphenyl)prop-2-yn-1-one 
• 54519-18-5 4,4'-dimethoxydibenzoylmethane 
• 70501-72-3 (4-methoxyphenyl)[5-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl]methanone 

Relevant academic research and scientific papers

Palladium-Catalyzed Oxidative C≡C Triple Bond Cleavage of 2-Alkynyl Carbonyl Compounds Toward 1,2-Dicarbonyl Compounds?

A new, general palladium-catalyzed oxidative strategy for the cleavage of the C≡C triple bond is presented. By employing PdCl2, CuBr2, TEMPO and air as the catalytic system and H2O as the carbonyl oxygen atom source, a wide range of 2-alkynyl carbonyl compounds, including 1,3-disubstituted prop-2-yn-1-ones, propiolamides and propiolates, lost an alkynyl carbon to access various 1,2-dicarbonyl compounds, e.g., 1,2-diones, 2-keto amides and 2-keto esters, through Wacker oxidation, intramolecular cyclization and C—C bond cleavage cascades.

Alkynyl?B(dan)s in Various Palladium-Catalyzed Carbon?Carbon Bond-Forming Reactions Leading to Internal Alkynes, 1,4-Enynes, Ynones, and Multiply Substituted Alkenes

It was found that the C(sp)?B(dan) bond of alkynyl?B(dan)s can be directly used for palladium-catalyzed carbon?carbon bond-forming reactions with aryl(alkenyl) halides and allylic carbonates as electrophiles, thus delivering unsymmetrical internal alkynes and unconjugated 1,4-enynes, respectively. With acyl chlorides as electrophiles, ynone synthesis is also promoted by a palladium catalyst with the assistance of a copper co-catalyst. These reactions can be achieved as more convenient one-pot reactions, without isolating the alkynyl?B(dan) formed in situ by the zinc-catalyzed dehydrogenative borylation of alkynes with HB(dan). In addition to direct C(sp)?B(dan) bond transformations, the C≡C bond in an alkynyl?B(dan) proved to be a promising scaffold for the construction of a multisubstituted alkene, which is synthesized by diboration of the C≡C?B(dan) moiety, leading to a triborylalkene followed by iterative regio- and stereoselective Suzuki?Miyaura cross-coupling reactions. As one example, the synthesis of the ethene with four different aryl groups, p-MeC6H4, p-MeOC6H4, p-NCC6H4, and p-F3CC6H4, was attained in high overall yield of 64% in six steps starting from the terminal alkyne, p-MeC6H4C≡CH. Besides these synthetic applications of the alkynyl?B(dan), the scope of the alkynyl substrate in the zinc-catalyzed dehydrogenative borylation was expanded to enhance the reliability as a provider of the alkynyl?B(dan). Consequently, 42 alkynes were found to participate in the dehydrogenative borylation as substrates; these are alkyl-, alkenyl-, aryl-, heteroaryl-, ferrocenyl-, silyl-, and borylalkynes, with or without a variety of functional groups. Lastly, a new method for preparing HB(dan), as a sulfide-free, cost-saving, and reaction-time-saving route, is disclosed. (Figure presented.).

Synthesis of 4,5-disubstituted-1H-1,2,3-triazoles

Abstract: Two-step procedure, a palladium catalyzed Sonogashira cross-coupling reaction of aroyl chlorides with aryl acetylenes, and 1,3-dipolar cycloaddition of the 1,3-diarylprop-2-yn-1-ones with sodium azide under catalyst free conditions achieved the

Synthesis and photophysical properties of 3,5-diaryl-2-heteroarylthiophenes

A series of 3,5-diaryl-2-heteroarylthiophenes have been synthesized via Fiesselmann type reaction between alkynones and easily available heteroarylmethanethiols or heteroarylmethyl carbamimidothioates. A correlation between compounds structure and efficie

Emission solvatochromic, solid-state and aggregation-induced emissive α-pyrones and emission-tuneable 1H-pyridines by Michael addition–cyclocondensation sequences

Starting from substituted alkynones, α-pyrones and/or 1H-pyridines were generated in a Michael addition–cyclocondensation with ethyl cyanoacetate. The peculiar product formation depends on the reaction conditions as well as on the electronic substitution

The first total synthesis of anemarchalconyn and anemarcoumarin A

Anemarchalconyn (1) and anemarcoumarin A (2), the natural bioactive compounds isolated from the rhizomes of Anemarrhena asphodeloides Bunge (Liliaceae), were first totally synthesized using easily available materials in short, convenient routes with overall yields of 32 and 48%.

Phosphinito palladium(ii) complexes as catalysts for the synthesis of 1,3-enynes, aromatic alkynes and ynones

An air-stable phosphinito palladium(ii) complex (Ph1-Phoxide) has been found to be an efficient catalyst in the formation of C-C bonds. The coupling of terminal alkynes formed gem-1,3-enynes as the only reaction products. Aromatic alkynes can be synthesized from the coupling of terminal alkynes and haloaromatic compounds (Sonogashira coupling). The phosphinito palladium(ii) complex also catalyses the coupling between acyl chlorides and terminal alkynes (Sonogashira coupling), furnishing ynones in excellent yields.

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.

Method for preparing alpha, beta-acetylenic ketone compounds through carbon monoxide-releasing molecular carbonylation carbon-carbon bond coupling

The invention discloses a method for preparing alpha, beta-acetylenic ketone compounds through carbon monoxide-releasing molecular carbonylation carbon-carbon bond coupling. According to the method, CO gas is not used, and the method comprises the followi

A highly efficient heterogeneous palladium-catalyzed cascade three-component reaction of acid chlorides, terminal alkynes and hydrazines leading to pyrazoles

In the presence of 0.5 mol% of 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized palladium(II) complex [MCM-41-2N-Pd(OAc)2] and 1.0 mol% of CuI, acid chlorides were coupled with terminal alkynes in Et3N at 50 °C to give α,β-unsaturated ynones, which were converted in situ into pyrazoles by the cycloaddition of hydrazines at room temperature with acetonitrile as cosolvent. The cascade reactions generated a variety of pyrazole derivatives in moderate to good yields, and this heterogeneous palladium catalyst exhibited higher catalytic activity than PdCl2(PPh3)2 and could be recovered and reused for at least 10 consecutive trials without any decreases in activity.