333754-59-9

Upstream product

• 536-74-3 phenylacetylene 
• 41398-67-8 2-phenylethynylanisole 
• 1188474-17-0 1-(but-2-yn-1-yloxy)-2-iodobenzene 
• 41876-99-7 1-iodo-2-(2-propynyloxy)benzene 
• 28557-00-8 phenylzinc chloride 
• 533-58-4 2-Iodophenol 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 

Relevant academic research and scientific papers

Iridium-Catalyzed Intramolecular Methoxy C?H Addition to Carbon–Carbon Triple Bonds: Direct Synthesis of 3-Substituted Benzofurans from o-Methoxyphenylalkynes

Catalytic hydroalkylation of an alkyne with methyl ether was accomplished. Intramolecular addition of the C?H bond of a methoxy group in 1-methoxy-2-(arylethynyl)benzenes across a carbon–carbon triple bond took place efficiently either in toluene at 110 °C or in p-xylene at 135 °C in the presence of an iridium catalyst. The initial 5-exo cyclization products underwent double-bond migration during the reaction to give 3-(arylmethyl)benzofurans in high yields.

Influence of the acetylenic substituent on the intramolecular carbolithiation of alkynes

The intramolecular carbolithiation of a series of propargylic ethers has been performed to evaluate the influence of the terminal substituent on the efficiency and the stereochemical outcome of the cyclization. Our results show that only 5-exo-dig cyclizations are observed, and dihydrobenzofurans are obtained exclusively. Depending on the nature of the terminal substituent, two cases can be considered. If the terminal substituent carried by the acetylenic carbon atom is itself a carbon atom, the cyclization can occur provided the terminal propargylic position bears a coordinating element and is at least disubstituted. When the cyclization occurs, it follows an anti-carbolithiation pathway and thus leads to the E isomer of the exocyclic double bond. Only in one case (Ph) was a mixture of the E and Z isomers of the resulting olefin recovered. The cyclization can also take place if the alkyne is directly substituted by S or Si, provided the cyclization conditions are tuned. In the case of the trimethylsilyl substituent, a syn-carbolithiation was observed. If the double bond is recovered, in most cases, in the exocyclic position, the products can aromatize directly for SPh-substituted substrate 24. Furthermore, in the two latter cases, when alkylation of the vinyllithium intermediate is performed, isomerization of the double bond seems instantaneous. Copyright

Synthetic applications of the nickel-catalyzed cyclization of alkynes combined with addition reactions in a domino process

Carbonickelations of alkynes and functionalization of the resulting vinylnickel moiety have been performed efficiently in a nickel-catalyzed domino cyclization-condensation process. This reaction, which does not require the preparation of any other organometallic reagent, proceeds only by exo-dig cyclization. This convenient and mild method constitutes a one-pot synthesis of substituted dihydrobenzofurans, chromans, isochromans, indoles, or indanes. Theses valuable products are generally obtained in good yields and high stereoselectivity. They are shown to be useful synthons for rapid access to functionalized polycyclic skeletons. Yes nickel can! Carbonickelation of alkynes and functionalization of the resulting vinylnickel moiety occurs efficiently. Overall, a domino cyclization-condensation process propagated by substoichiometric nickel catalysis takes place (see scheme). This one-pot synthesis provides substituted polyheterocyclic compounds in good yields and high stereoselectivity.

Heterocyclization by catalytic carbonickelation of alkynes: A domino sequence involving vinylnickels

Reaction of Ni(0) in the presence of iodoarylethers 1 leads, after syn intramolecular carbonickelation of the triple bond, to nucleophilic vinylnickels which can be trapped, in a tandem process, by various electrophiles introduced at the onset of the reac

Bowl-shaped tris(2,6-diphenylbenzyl)tin hydride: A unique reducing agent for radical and ionic chemistry

Unique selectivity, hitherto not observable in ordinary radical and ionic reactions, is achieved with the bowl-shaped tris(2,6-diphenylbenzyl)tin hydride (TDTH; see structure), which has been successfully utilized as a new reducing agent.

STEREOSELECTIVE SYNTHESIS OF (Z)-2,3-DIHYDRO-3-(ARYLMETHYLENE)BENZOFURANS VIA THE PALLADIUM CATALYSED INSERTION AND CROSS COUPLING REACTION OF 1-IODO-2-(2-PROPYNYLOXY)BENZENE AND ARYLZINC CHLORIDE

The title compound was prepared in fair to good yields from 1-iodo-2-(2-propynyloxy)benzene and arylzinc chloride via tandem insertion and cross coupling reaction catalysed by pertinent palladium catalyst, such as palladium acetate and triphenylphosphine.