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Upstream product

• 628-71-7 1-Heptyne 
• 106-38-7 para-bromotoluene 
• 624-31-7 4-tolyl iodide 
• 693-02-7 hex-1-yne 
• 627885-28-3 dimethyl-(1-heptynyl)silanol 
• 5720-05-8 4-methylphenylboronic acid 
• 5663-96-7 oct-2-ynoic acid 
• 54573-13-6 1-iodo-hept-1-yne 
• 19821-84-2 1-bromohept-1-yne 
• 17873-01-7 (4-methylphenyl)trimethoxysilane 
• 66-25-1 hexanal 
• 766-97-2 4-n-methylphenylacetylene 
• 2400-59-1 dihexanoyl peroxide 
• 106-43-4 para-chlorotoluene 

Relevant academic research and scientific papers

CuI/PPh3/PEG-Water: An efficient catalytic system for cross-coupling reaction of aryl iodides and alkynes

An efficient protocol for the copper-catalyzed Sonogashira coupling of aryl iodides with terminal acetylenes in water-polyethylene glycol has been established. Both electron-rich and electron-deficient aryl iodides were arylalkynated under microwave heating or reflux in oil bath to afford good to excellent yields. Copyright

Palladium-free copper-catalyzed coupling reaction of aryl iodides and terminal acetylenes in water

An efficient and general method has been developed for palladium-free copper-catalyzed cross-coupling reactions of aryl iodides and terminal acetylenes under microwave irradiation in water, producing various alkynes in excellent yields. This process can also be successfully carried out under reflux in an oil bath. Copyright Taylor & Francis Group, LLC.

Efficient copper-free PdCl2(PCy3)2- catalyzed sonogashira coupling of aryl chlorides with terminal alkynes

Under copper-free conditions and with Cs2CO3 as a base, PdCl2(PCy3)2 showed high catalytic activity for cross-coupling of electron-rich, elctron-neutral, and electron-deficient aryl chlorides with a variety of terminal alkynes in DMSO at 100-120 °C affording internal arylated alkynes in good to excellent yields.

Facile synthesis of substituted alkynes by cyclopalladated ferrocenylimine catalyzed cross-coupling of arylboronic acids/esters with terminal alkynes

A highly efficient and convenient catalytic system for the cross-coupling reaction of arylboronic reagents with terminal alkynes was described by using cyclopalladated ferrocenyhmine (I)/silver oxide as the catalyst at room temperature. This method provides the first examples of a palladacycle-catalyzed cross-coupling reaction of arylboronic acids/esters with terminal alkynes under mild conditions, and also a facile route for the synthesis of substituted alkynes with a low Pd loading of 1 mol-%. The substrates could be extended to electron-poor alkynes, for which the traditional Sonogashira reaction does not proceed. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Copper-catalyzed decarboxylative coupling of aryl halides with alkynyl carboxylic acids performed in water

Most alkynes are volatile liquids, which are relatively difficult to use and to transport. In contrast, alkynyl carboxylic acids offer a stable and attractive alternative for the alkynylation reactions. Here, we employed alkynyl carboxylic acids as reaction partners for the alkynylation of aryl halides. Copper-catalyzed decarboxylative coupling, including various challenging aryl bromides with phenylpropiolic acid, was performed in water without using co-solvents with good yields. Our approach provides a low-loading, low-cost, stable and environmentally friendly copper catalyst system for decarboxylative coupling.

Efficient palladium-catalyzed cross-coupling reaction of alkynyl halides with organoboronic acids under aerobic conditions

Ligand-free palladium-catalyzed cross-coupling reaction of alkynyl halides with organoboronic acids under aerobic conditions has been developed. In the presence of bis(dibenzylideneacetone)palladium(0) and cesium carbonate, a variety of alkynyl halides (I, Br, and Cl) underwent the Suzuki-Miyaura cross-coupling reaction with organoboronic acids at room temperature to afford the corresponding unsymmetrical diarylalkynes in moderate to good yields. It is noteworthy that this is first report on the reaction of alkynyl chlorides with arylboronic acids. Georg Thieme Verlag Stuttgart · New York.

Copper-catalysed photoinduced decarboxylative alkynylation: a combined experimental and computational study

Redox-active esters (RAEs) as alkyl radical precursors have demonstrated great advantages for C-C bond formation. A decarboxylative cross-coupling method is described to afford substituted alkynes from various carboxylic acids using copper catalysts CuCl and Cu(acac)2. The photoexcitation of copper acetylides with electron-rich NEt3as a ligand provides a general strategy to generate a range of alkyl radicals from RAEs of carboxylic acids, which can be readily coupled with a variety of aromatic alkynes. The scope of this cross-coupling reaction can be further expanded to aliphatic alkynes and alkynyl silanes using a catalytic amount of preformed copper-phenylacetylide. In addition, DFT calculations revealed the favorable reaction pathway and that the bidentate acetylacetonate ligand of the copper intermediate plays an important role in inhibiting the homo-coupling of the alkyne.

Multi-Metal-Catalyzed Oxidative Radical Alkynylation with Terminal Alkynes: A New Strategy for C(sp3)-C(sp) Bond Formation

A new way for C(sp3)-C(sp) cross-coupling with terminal alkynes has been developed by using a multi-metal-catalyzed reaction strategy. Alkyl radicals generated from different approaches are able to couple with terminal alkynes by judicious selection of the catalyst combination. This reaction protocol offers an efficient alternative approach for the synthesis of substituted alkynes from terminal alkynes besides traditional Sonogashira coupling. Mechanistic studies have also been carried out to clarify the role of each metal catalyst in the radical alkynylation processes. The reactions were found to go through radical reaction pathways. Synergistic cooperation of the metal catalysts is the key for controlling the reaction selectivity of alkyl radicals toward C(sp3)-C(sp) bond formation.

Ferrocenyl bisoxazoline as an efficient non-phosphorus ligand for palladium-catalyzed copper-free Sonogashira reaction in aqueous solution

Pd(OAc)2-catalyzed Sonogashira coupling reactions of alkynes and a variety of aryl halides with 1,3-bis(5-ferrocenylisoxazoline-3-yl)benzene as an efficient non-phosphorus ligand under copper-free conditions are presented. The main advantages over previous methodologies include low catalyst loading (0.2 mol% Pd(OAc)2 and 0.4 mol% ferrocenyl bisoxazoline ligand are sufficient for these coupling reactions), less problematic reaction medium (water–dimethylformamide) and more convenient operation (no requirement for nitrogen protection).

Copper-Catalyzed Decarboxylative Alkylation of Terminal Alkynes

A copper-catalyzed decarboxylative alkylation of terminal alkynes under mild reaction conditions has been reported. Various alkyl diacyl peroxides were applied as the alkyl source for the formation of C(sp3)?C(sp) bond. A range of terminal alkynes including aryl alkynes and alkyl alkynes delivered the alkylated internal alkynes with good to high performances. Mechanism studies suggested that this reaction involves a free radical pathway. (Figure presented.).