1220698-84-9

Upstream product

• 1220698-64-5 1-(4-methoxyphenyl)-5-phenyl-1-pentyn-3-yl formate 
• 696-62-8 para-iodoanisole 
• 1823-14-9 5-phenyl-1-pentyne 
• 100-52-7 benzaldehyde 
• 5281-18-5 benzaldehyde, hydrazone 
• 55088-86-3 1-(but-3-en-1-yn-1-yl)-4-methoxybenzene 
• 66950-73-0 3-phenylpropyl 1-trifluoromethanesulfonate 
• 768-60-5 4-methoxyphenylacetylen 
• 122-97-4 3-Phenyl-1-propanol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 33675-41-1 1-bromo-2-(4-methoxyphenyl)acetylene 

Downstream Products

• 2046-18-6 4-phenylbutyronitrile 
• 874-90-8 4-methoxybenzonitrile 
• 1216563-29-9 N-(4-methoxyphenyl)-5-phenylpentanamide 
• 103304-55-8 6,7-dihydro-8-phenyl-9-(4-methoxyphenyl)-5H-benzocycloheptene 
• 21855-86-7 6,7-dihydro-9-(4-methoxyphenyl)-5H-benzocycloheptene 

Relevant academic research and scientific papers

Enabling the Use of Alkyl Thianthrenium Salts in Cross-Coupling Reactions by Copper Catalysis

Alkyl groups are one of the most widely used groups in organic synthesis. Here, a a series of thianthrenium salts have been synthesized that act as reliable alkylation reagents and readily engage in copper-catalyzed Sonogashira reactions to build C(sp3)?C(sp) bonds under mild photochemical conditions. Diverse alkyl thianthrenium salts, including methyl and disubstituted thianthrenium salts, are employed with great functional breadth, since sensitive Cl, Br, and I atoms, which are poorly tolerated in conventional approaches, are compatible. The generality of the developed alkyl reagents has also been demonstrated in copper-catalyzed Kumada reactions.

Switch in Selectivity for Formal Hydroalkylation of 1,3-Dienes and Enynes with Simple Hydrazones

Controlling reaction selectivity is a permanent pursuit for chemists. Regioselective catalysis, which exploits and/or overcomes innate steric and electronic bias to deliver diverse regio-enriched products from the same starting materials, represents a powerful tool for divergent synthesis. Recently, the 1,2-Markovnikov hydroalkylation of 1,3-dienes with simple hydrazones was reported to generate branched allylic compounds when a nickel catalyst was used. As part of the effort, shown here is that a complete switch of Markovnikov to anti-Markovnikov addition is obtained by changing to a ruthenium catalyst, thus providing direct and efficient access to homoallylic products exclusively. Isotopic substitution experiments indicate that no reversible hydro-metallation across the metal-π-allyl system occurred under ruthenium catalysis. Moreover, this protocol is applicable to the regiospecific hydroalkylation of the distal C=C bond of 1,3-enynes.

Diastereodivergent Reductive Cross Coupling of Alkynes through Tandem Catalysis: Z- and E-Selective Hydroarylation of Terminal Alkynes

A diastereodivergent hydroarylation of terminal alkynes is accomplished using tandem catalysis. The hydroarylation allows highly selective synthesis of both E and Z diastereoisomers of aryl alkenes, from the same set of starting materials, using the same combination of palladium and copper catalysts. The selectivity is controlled by simple changes in the stoichiometry of the alcohol additive. The hydroarylation has excellent substrate scope and can be accomplished in the presence of various classes of compounds, including esters, nitriles, alkyl halides, epoxides, carbamates, acetals, ethers, silyl ethers, and thioethers. The Z-selective hydroarylation is accomplished using a new approach based on tandem Sonogashira coupling and catalytic semireduction. The E-selective hydroarylation involves an additional catalytic isomerization of the Z-alkene. Our explorations of the reaction mechanism explain the role of individual reaction components and how the subtle changes in the reaction conditions influence the rates of specific steps of the hydroarylation. Our studies also show that, although the Z- and E-selective hydroarylation reactions are mechanistically closely related, the roles of the palladium and copper catalysts in the two reactions are different.

Transmetalation of Alkylzirconocenes in Copper-Catalyzed Alkyl–Alkynyl Cross-Coupling Reactions

A simple copper-catalyzed alkyl–alkynyl cross-coupling strategy has been developed using the reaction between alkynyl bromides and alkylzirconocenes. The alkylzirconocenes were generated in situ via regioselective addition of Schwartz's reagent (ZrCp2HCl) on to alkenes. The reaction has a broad scope, a range of functionalized bromoalkynes and alkylzirconium reagents were successfully coupled, resulting in moderate to good yields of the desired internal alkynes. (Figure presented.).

Splitting a Substrate into Three Parts: Gold-Catalyzed Nitrogenation of Alkynes by C-C and C≡C Bond Cleavage

A gold-catalyzed nitrogenation of alkynes for the synthesis of carbamides and amino tetrazoles through C-C and C≡C bond cleavages is described. A diverse set of functionalized carbamide and amino tetrazole derivatives were selectively constructed under mild conditions. The chemoselectivity can be easily switched by the selection of the acid additives. The reaction is characterized by its broad substrate scope, direct construction of high value products, easy operation under air, and mild conditions at room temperature. This chemistry provides a way to transform alkynes by splitting the substrate into three parts.

Copper-catalyzed endo-type trifluoromethylarylation of alkynes

A new copper-catalyzed trifluoromethylarylation reaction of alkynes has been developed. The transformation represents the first example of endo-type carbotrifluoromethylation of unsaturated carbon-carbon bonds and provides efficient access to a variety of

Copper-catalyzed carboarylation of alkynes via vinyl cations

Copper-catalyzed arylation of electron rich alkynes reveals stabilized trisubstituted vinyl cation equivalents that react with pendant arene nucleophiles to form all carbon tetrasubstituted alkenes. The new process streamlines the synthesis of important medicinally relevant molecules.

Selective synthesis of allenes and alkynes through ligand-controlled, palladium-catalyzed decarboxylative hydrogenolysis of propargylic formates

Ligand-controlled regioselective palladium-catalyzed decarboxylative hydrogenolysis of propargylic formates is described. A wide range of allenes and alkynes were obtained by using either 1,2-diphenylphosphinoethane (DPPE) or 1,6-bisdiphenylphosphinohexane (DPPH) as a catalyst ligand.