872471-04-0

Upstream product

• 628-71-7 1-Heptyne 
• 577-19-5 2-nitrophenyl bromide 
• 609-73-4 o-nitroiodobenzene 

Downstream Products

• 149731-55-5 1-((E)-Hept-1-enyl)-2-nitro-benzene 
• 69561-06-4 1-(2-aminophenyl)-heptan-1-one 
• 1257998-57-4 1-(benzo[c]isoxazol-3-yl)hexan-1-one 

Relevant academic research and scientific papers

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).

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.

One-Pot Synthesis of Indole Derivatives from the Reaction of Nitroalkynes and Alkynes via a Mercury-Carbene Intermediate

The cyclization of nitroalkyne catalyzed by Hg(OTf) 2 to produce the corresponding benzo[ c ]isoxazole in excellent yields with high selectivity is reported. On the basis of this strategy, a one-pot method to synthesize indole derivatives has been developed. In this transformation, two Hg-carbene intermediates are proposed to be involved..

Synthesis and Simple Immobilization of Palladium(II) Acyclic Diaminocarbene Complexes on Polystyrene Support as Efficient Catalysts for Sonogashira and Suzuki-Miyaura Cross-Coupling

Immobilization of palladium(II) acyclic diaminocarbene (Pd(II)-ADC) complexes on a resin support surface has been easily performed by metal-mediated addition of amino groups of benzhydrylamine-polystyrene to the coordinated isocyanide ligand of cis-PdCl2(CNR)2 (R = t-Bu, Cy). The investigation of the benzhydrylamine reaction with palladium-coordinated isocyanides in solution has revealed that, depending on the reaction conditions, two carbene-type complexes can be obtained as a result of the addition to the CN triple bond, as well as a third complex which is formed via substitution of the isocyanide ligand by benzhydrylamine. Nucleophilic addition of an amino group to the isocyanide ligand has led to a cis-acyclic diaminocarbene complex or a cationic diaminocarbene complex with trans configuration and an intramolecular hydrogen-bonded chloride anion (the nature of this noncovalent interaction was analyzed by DFT calculations, including AIM analysis). The unsupported and resin-supported palladium catalysts have demonstrated high catalytic activity in both Sonogashira and Suzuki-Miyaura cross-coupling. The supported catalyst can be recovered and repeatedly reused without a significant loss in efficiency. The degree of the palladium binding with polystyrene, the oxidation state, and the palladium leaching level were investigated by XPS and XRF analyses.

A combined experimental and density functional theory study on the Pd-mediated cycloisomerization of o-alkynylnitrobenzenes - Synthesis of isatogens and their evaluation as modulators of ROS-mediated cell death

Highly selective cycloisomerization of o-alkynylnitrobenzenes, leading to isatogens, has been achieved by employment of a PdII complex. This reaction is very general and functional-group-tolerant. The possible mechanism of this reaction was inv

A highly effective one-pot synthesis of quinolines from 2-alkynylnitrobenzenes

A highly effective one-pot synthesis of poly-substituted quinolines from 2-alkynylnitrobenzenes using inexpensive reagents has been developed. Reaction of 2-alkynylnitrobenzenes with Sn/HCl in EtOH resulted in the formation of 2-aminophenyl ketones and subsequently condensed in situ with ketones to form tri-substituted quinolines in 80-97% yields.

Platinum oxide catalyzed hydrosilylation of unsymmetrical internal aryl alkynes under ortho-substituent regiocontrol

(Chemical Equation Presented) PtO2- and H2PtCl 6-catalyzed hydrosilylation of internal aryl alkynes having a para or an ortho substituent with triethylsilane are discussed and compared. The regioselectivity of the H-Si bond addition was found to be controlled by the ortho substituent rather than the nature of the platinum catalyst. Arylalkynes with an ortho substituent, regardless of its electronic nature, directed the silyl substituent mainly to the α-position. PtO2 proved to be a versatile and powerful catalyst compared to H2PtCl6 since it prevents the alkyne reduction.