5293-78-7

Upstream product

• 529-28-2 4-iodoanisol 
• 1066-54-2 trimethylsilylacetylene 
• 6706-92-9 2,2'-dimethoxybenzil 
• 578-57-4 2-bromoanisole 
• 471-25-0 Propiolic acid 
• 142-45-0 Acetylenedicarboxylic acid 
• 994-71-8 bis(tributylstannyl)acetylene 
• 5293-93-6 β,β-bis(o-methoxyphenyl)vinyl bromide 
• 186581-53-3 diazomethane 
• 93533-83-6 2,2′-(ethyne-1,2-diyl)diphenol 
• 4301-14-8 acetylenemagnesium bromide 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 56-23-5 tetrachloromethane 
• 90585-33-4 2,2'-dimethoxybenzil dihydrazone 

Downstream Products

• 28238-45-1 methyl 2-(2-methoxyphenyl)benzo[b]furan-3-carboxylate 
• 1564265-70-8 ethyl 4,5-bis(2-methoxyphenyl)-3-oxo-2-phenylcyclopenta-1,4-dienecarboxylate 
• 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 
• 1402170-18-6 C₁₈H₁₄O₄ 
• 1402215-58-0 C₅₄H₄₃NO₄ 

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.

Palladium nanoparticles catalyzed Sonogashira reactions for the one-pot synthesis of symmetrical and unsymmetrical diarylacetylenes

A variety of symmetrical and unsymmetrical diarylacetylenes are synthesized by ligand-free palladium nanoparticles catalyzed copper-free and amine-free Sonogashira cross-coupling reactions between aryl iodides and trimethylsilylacetylene (TMSA) under mild reaction conditions.