5293-78-7

Upstream product

• 186581-53-3 diazomethane 
• 93533-83-6 2,2′-(ethyne-1,2-diyl)diphenol 
• 5293-93-6 β,β-bis(o-methoxyphenyl)vinyl bromide 
• 529-28-2 4-iodoanisol 
• 994-71-8 bis(tributylstannyl)acetylene 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 4301-14-8 acetylenemagnesium bromide 
• 60-29-7 diethyl ether 
• 7664-41-7 ammonia 
• 56-23-5 tetrachloromethane 
• 90585-33-4 2,2'-dimethoxybenzil dihydrazone 
• 66021-98-5 (o-methoxyphenyl)-1-propyne 
• 1066-54-2 trimethylsilylacetylene 
• 6706-92-9 2,2'-dimethoxybenzil 

Downstream Products

• 14310-34-0 1,2-bis(2-methoxyphenyl)ethane 
• 28238-45-1 methyl 2-(2-methoxyphenyl)benzo[b]furan-3-carboxylate 
• 42926-53-4 2-(2’-methoxyphenyl)benzofuran 
• 1224447-52-2 3-bromo-2-(2-methoxyphenyl)benzofuran 
• 1363821-86-6 2-(2-methoxyphenyl)benzofuran-3-carbonitrile 
• 1404432-63-8 1-(iodomethyl)-2,3-bis(2-methoxyphenyl)-1-methyl-1H-indene 
• 1402215-58-0 C₅₄H₄₃NO₄ 
• 1402215-59-1 C₆₄H₅₆N₂O₄ 
• 1402170-18-6 C₁₈H₁₄O₄ 
• 1469444-93-6 (Z)-1-methoxy-2-(2-phenyl-2-o-methoxyphenylvinyl)benzene 
• 1469445-24-6 (E)-1-methoxy-2-(2-phenyl-2-o-methoxyphenylvinyl)benzene 
• 1564265-70-8 ethyl 4,5-bis(2-methoxyphenyl)-3-oxo-2-phenylcyclopenta-1,4-dienecarboxylate 
• 40230-91-9 [(2-methoxyphenyl)ethynyl]trimethylsilane 

Relevant academic research and scientific papers

Rhodium-Catalyzed Regioselective Hydroformylation of Alkynes to α,β-Unsaturated Aldehydes Using Formic Acid

A rhodium-catalyzed hydroformylation of alkynes with formic acid was developed. The method provides α,β-unsaturated aldehydes in high yield and E-selectivity without the need to handle toxic CO gas.

Rhodium-Catalyzed Spiro Indenyl Benzoxazine Synthesis via C-H Activation/Annulation of 3-Aryl-2H-Benzo[b][1,4]oxazines and Alkynes

The rhodium (III)-catalyzed annulation of 3-Aryl-2H-Benzo[b][1,4]oxazines with alkynes via C–H activation has been developed. This reaction afforded a series of spiro indenyl benzoxazine in high yields under mild reaction condition with good functional group tolerance.

Diborative Reduction of Alkynes to 1,2-Diboryl-1,2-Dimetalloalkanes: Its Application for the Synthesis of Diverse 1,2-Bis(boronate)s

Reduction of alkynes with alkali metals in the presence of B2pin2 results in diboration of alkynes. Distinct from conventional dissolving metal hydrogenations, two carbon-boron bonds and also two carbon-alkali metal bonds can be constructed in one operation to form 1,2-diboryl-1,2-dimetalloalkanes. The 1,2-diboryl-1,2-dimetalloalkanes generated are readily convertible to a wide range of vicinal bis(boronate)s. In particular, oxidation of the 1,2-dianionic species provides (E)-1,2-diborylalkenes, unique anti-selective diboration of alkynes being thus executed.

Rhodium(III)-catalysed decarbonylative annulation through C-H activation: Expedient access to aminoisocoumarins by weak coordination

Rhodium-catalysed decarbonylative annulation of isatoic anhydrides with alkynes through C-H activation for the synthesis of aminoisocoumarins was developed. This enables the gram-scale transformation to iodoisocoumarin which is a vital building block in transition-metal-catalysed cross couplings. These compounds exhibit blue-emitting luminescence properties.

Direct Synthesis of Symmetric Diarylethynes from Calcium Carbide and Arylboronic Acids/Esters

A new methodology for the direct synthesis of symmetric diarylethynes from the reactions of calcium carbide with arylboronic acids/esters is described. Various symmetric diarylethynes were generated from the corresponding arylboronic acids/esters in satisfactory yield by using a palladium catalyst. The advantages of this protocol include the use of a readily available and easy-to-handle acetylene source, and a simple work-up procedure.

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.

Palladium-Catalyzed Domino Process: Synthesis of Symmetrical Diarylalkynes, cis- and trans-Alkenes using Lithium Acetylide as a Synthon

An efficient domino protocol has been developed for the synthesis of symmetrical diarylalkynes. Notably, the method was successful in the presence of a palladium catalyst without the support of a copper co-catalyst. Significantly, the method enabled the use of the commercially available and cheap lithium acetylide ethylenediamine complex as a source of acetylene for the construction of dual C-C bonds, with a wide range of compatibility towards various substituents of the aryl bromides/iodides. Significantly, this protocol was successfully applied to the synthesis of cis- and trans-alkenes in a highly stereoselective manner in a sequential one-pot process.

Catalysts for the alkyne metathesis

Organometallic compounds of the general formula (I), in which M=Mo, W, are claimed.

Rhodium-Catalyzed C-H Annulation of Nitrones with Alkynes: A Regiospecific Route to Unsymmetrical 2,3-Diaryl-Substituted Indoles

The direct C-H annulation of anilines or related compounds with internal alkynes provides straightforward access to 2,3-disubstituted indole products. However, this transformation proceeds with poor regioselectivity in the synthesis of unsymmetrically 2,3-diaryl substituted indoles. Herein, we report the rhodium(III)-catalyzed C-H annulation of nitrones with symmetrical diaryl alkynes as an alternative method to prepare 2,3-diaryl-substituted N-unprotected indoles with two different aryl groups. One of the aryl substituents is derived from N?C-aryl ring of the nitrone and the other from the alkyne substrate, thus providing the indole products with exclusive regioselectivity.

Direct observation of reduction of Cu(II) to Cu(I) by terminal alkynes

X-ray absorption spectroscopy and in situ electron paramagnetic resonance evidence were provided for the reduction of Cu(II) to Cu(I) species by alkynes in the presence of tetramethylethylenediamine (TMEDA), in which TMEDA plays dual roles as both ligand and base. The structures of the starting Cu(II) species and the obtained Cu(I) species were determined as (TMEDA)CuCl2 and [(TMEDA)CuCl]2 dimer, respectively.