144304-05-2

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 89343-06-6 tris-iso-propylsilyl acetylene 
• 623-12-1 4-chloromethoxybenzene 
• 696-62-8 para-iodoanisole 
• 111409-79-1 1-bromo-2-(triisopropylsilyl)acetylene 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 701-53-1 p-methoxybenzoyl fluoride 
• 100-66-3 methoxybenzene 
• 6485-79-6 chlorotriisopropylsilane 
• 768-60-5 4-methoxyphenylacetylen 
• 100-07-2 4-methoxy-benzoyl chloride 
• 100-09-4 4-methoxybenzoic acid 
• 2227-57-8 3-(4-methoxyphenyl)propynoic acid 

Relevant academic research and scientific papers

A copper- and amine-free Sonogashira-type coupling procedure catalyzed by oxime palladacycles

Oxime palladacycle derived from 4,4′-dichlorobenzophenone was found to promote the Sonogashira reaction of aryl iodides and aryl bromides with terminal acetylenes using 1 equivalent of tetrabutylammonium acetate in organic solvents generally in 1 h at 110

Regio-selective cyanation of (Z)-(1,2-dibromo-2-arylvinyl)triisopropylsilane with suppression of halogen elimination

Highly regio-selective cyanation of vicinal (Z)-dibromoalkenyl silanes was achieved by a vinylic Rosenmund-von Braun reaction, significantly suppressing side-production of alkyne. The alkyne was generated by a halogen elimination side-reaction that is an intrinsic problem in metal-activation of vicinal dihaloalkenes. We have studied to overcome the problem, and finally found the combination of CuCN and O?=?PPh3 in toluene solvent effectively controlled the production of byproducts. The resultant single isomer has significance in potentially application as a multi-tunable synthetic scaffold.

Rapid synthesis of crowded aromatic architectures from silyl acetylenes

Congested aromatic systems were prepared by benzannulating silyl-protected arylacetylenes. The silyl groups may be retained in the naphthalene products and transformed into iodides in high yield. The desirable attributes of this strategy, particularly its remarkable tolerance of sterically hindered alkynes, are showcased in the efficient synthesis of a congested, branched oligo(naphthalene). As such, benzannulations of diaryl and silyl-protected acetylenes show outstanding promise for accessing new aromatic architectures.

Electro-alkynylation: Intramolecular Rearrangement of Trialkynylorganoborates for Chemoselective C(sp2)-C(sp) Bond Formation

An alternative and complementary transformation for the synthesis of aryl- and heteroaryl-substituted alkynes is presented that relies on a chemoselective electrocoupling process. Tetraorganoborate substrates were logically designed and simply accessed by transmetalations using readily or commercially available organotrifluoroborate salts.

Nickel-Catalyzed Decarbonylative Alkynylation of Acyl Fluorides with Terminal Alkynes under Copper-Free Conditions

Nickel-catalyzed decarbonylative alkynylation of acyl fluorides with terminal silylethynes under copper-free conditions is described. This newly developed method has a wide substrate scope, affording internal silylethynes in moderate to high yields. The formation of 1,3-diynes as homocoupled products and conjugate enones as carbonyl-retentive products were effectively suppressed.

Sterically Controlled Late-Stage C-H Alkynylation of Arenes

Phenylacetylenes are key structural motifs in organic chemistry, which find widespread applications in bioactive molecules, synthetic intermediates, functional materials, and reagents. These molecules are typically prepared from prefunctionalized starting materials, e.g. using the Sonogashira coupling, or using directing group-based C-H activation strategies. While highly efficient, these approaches remain limited by their inherent selectivities for specific regioisomers. Herein we present a complementary approach based on an arene-limited nondirected C-H activation. The reaction is predominantly controlled by steric rather than electronic factors and thereby gives access to a complementary product spectrum with respect to traditional methods. A broad scope as well as the suitability of this protocol for late-stage functionalization are demonstrated.

Chemoselective Aerobic Cross-Dehydrogenative Coupling of Terminal Alkynes with Hydrosilanes by a Nanoporous Gold Catalyst

Aerobic cross-dehydrogenative coupling between terminal alkynes and hydrosilanes occurred in the presence of nanoporous gold catalyst under O2 atmosphere. A variety of alkynylsilanes were synthesized in good-to-high yields and the catalyst was easily recovered and reused many times. Furthermore, the chemoselective direct silyl protection of terminal acetylenes of alkynols over the hydroxyl groups was achieved with this catalytic system.

Oxine based unsymmetrical (O?, N, S/Se) pincer ligands and their palladium(ii) complexes: synthesis, structural aspects and applications as a catalyst in amine and copper-free Sonogashira coupling

Unsymmetrical pincer ligands having an 8-hydroxyquinoline (oxine) core viz. 2-(phenylthio/selenomethyl) quinolin-8-ol (L1/L2), 2-(N,N-dimethylthiocarbamoyl) quinolin-8-ol (L3) and 2-(pyrrolidin-1-ylthiocarbamoyl) quinolin-8-ol (L4) were synthesized. 2-Met

PALLADIUM COMPLEX, COUPLING REACTION USING THE PALLADIUM COMPLEX AND METHOD FOR PRODUCING ORGANIC ALKYNE COMPOUND USING THE COUPLING REACTION

PROBLEM TO BE SOLVED: To provide a novel palladium catalyst which can be used for synthesis of an organic alkyne compound, using an arylation agent having an ester group in place of halogenated aryl. SOLUTION: The present invention provides a palladium co

Amide to Alkyne Interconversion via a Nickel/Copper-Catalyzed Deamidative Cross-Coupling of Aryl and Alkenyl Amides

A nickel-catalyzed deamidative cross-coupling reaction of amides with terminal alkynes as coupling partners was disclosed. This newly developed methodology allows the direct interconversion of amides to alkynes and enables a facile route for C(sp2)-C(sp) bond formation in a straightforward and mild fashion.