1007-47-2

Upstream product

• 1184-58-3 dimethylaluminum chloride 
• 536-74-3 phenylacetylene 
• 75-24-1 trimethylaluminum 

Downstream Products

• 13141-42-9 2-(2-phenylethynyl)pyridine 
• 7380-78-1 4-(phenylethynyl)anisole 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 7338-94-5 1,3-diphenyl-2-propynone 
• 23566-47-4 5-methyl-1-phenyl-hex-1-yn-3-one 
• 6088-96-6 (penta-1,4-diynyl)benzene 
• 957061-24-4 (S_S,R)-N-(p-toluenesulfinyl)-1,3-diphenylprop-2-ynylamine 

Relevant academic research and scientific papers

Gold-Catalyzed Cascade Reaction of Skipped Diynes for the Construction of a Cyclohepta[b]pyrrole Scaffold

A gold-catalyzed cascade reaction of skipped diynes (1,4-diynes) and pyrroles has been developed. This reaction proceeds by the consecutive regioselective hydroarylation of two alkynes with a pyrrole, followed by a 7-endo-dig cyclization to give 1,6-dihydrocyclohepta[b]pyrroles in good yields. The direct synthesis of cyclohepta[b]indoles using indole nucleophiles has also been reported.

Rare-Earth Catalyzed C?H Bond Alumination of Terminal Alkynes

Organoaluminum reagents’ application in catalytic C?H bond functionalization is limited by competitive side reactions, such as carboalumination and hydroalumination. Herein, rare-earth tetramethylaluminate complexes are shown to catalyze the exclusive C?H bond metalation of terminal alkynes with the commodity reagents trimethyl-, triethyl-, and triisobutylaluminum. Kinetic experiments probing alkyl-group exchange between rare-earth aluminates and trialkylaluminum, C?H bond metalation of alkynes, and catalytic conversions reveal distinct pathways of catalytic aluminations with triethylaluminum versus trimethylaluminum. Most significantly, kinetic data point to reversible formation of a unique [Ln](AlR4)2?AlR3 adduct, followed by turnover-limiting alkyne metalation. That is, C?H bond activation occurs from a more associated organometallic species, rather than the expected coordinatively unsaturated species. These mechanistic conclusions allude to a new general strategy for catalytic C?H bond alumination that make use of highly electrophilic metal catalysts.

Room temperature lewis base-catalyzed alumination of terminal alkynes

An efficient and mild access to mixed dimethylalkynylaluminum reagents has been developed via a direct Lewis base-catalyzed alumination of terminal alkynes by trimethylaluminum. The use of bis(trimethylsilyl)methylamine enables the metalation at room temp

Continuous Flow Synthesis of Dimethylalkynylaluminum Reagents

A new process for the synthesis of dimethylalkynylaluminum reagents under flow conditions is described. It involves a base-catalyzed alumination of terminal alkynes using a resin-supported organocatalyst. Final organometallic species are obtained in solution, and can further react with various aldehydes or nitrones.

Highly Efficient Synthesis of 2-Substituted Benzo[ b ]furan Derivatives from the Cross-Coupling Reactions of 2-Halobenzo[ b ]furans with Organoalane Reagents

A highly efficient and simple route for the synthesis of 2-substituted benzo[ b ]furans has been developed by palladium-catalyzed cross-coupling reaction of 2-halobenzo[ b ]furans with aryl, alkynyl, and alkylaluminum reagents. Various 2-aryl-, 2-alkynyl-, and 2-alkyl-substituted benzo[ b ]furan derivatives can be obtained in 23-97% isolated yields using 2-3 mol% PdCl 2/4-6 mol% XantPhos as the catalyst under mild reaction conditions. The aryls bearing electron-donating or electron-withdrawing groups in 2-halobenzo[ b ]furans gave products in 40-97% isolated yields. In addition, aluminum reagents containing thienyl, furanyl, trimethylsilanyl, and benzyl groups worked efficiently with 2-halobenzo[ b ]furans as well, and three bioactive molecules with 2-substituted benzo[ b ]furan skeleton were synthesized. Furthermore, the broad substrates scope and the typical maintenance of vigorous efficiency on gram scale make this protocol a potentially practical method to synthesize 2-substituted benzo[ b ]furan derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.

Nickel-Catalyzed Allylmethylation of Alkynes with Allylic Alcohols and AlMe3: Facile Access to Skipped Dienes and Trienes

We present herein an unprecedented allylative dicarbofunctionalization of alkynes with allylic alcohols. This simple catalytic procedure utilizes commercially available Ni(COD)2, triphenylphosphine, and inexpensive reagents, and delivers valuable skipped dienes and trienes with an all-carbon tetrasubstituted alkene unit in a highly stereoselective fashion. Preliminary mechanistic studies support the reaction pathway of allylnickelation followed by transmetalation in this dicarbofunctionalization of alkynes.

Alkynylaluminum Synthesis Catalyzed by a Zwitterionic Neodymium(III) Heterobimetallic Compound

The reaction of H{PhB(OxMe2)2C5H5} (OxMe2 = 4,4-dimethyl-2-oxazoline) with Nd(AlMe4)3 (1) provides Me2Al{(OxMe2)2PhBCp}Nd(AlMe4)2

Stereoselective synthesis of medium-sized cyclic ethers: Application of C -glycosylation chemistry to seven- to nine-membered lactone-derived thioacetals and their sulfone counterparts

Stereoselective synthesis of α,α′-substituted medium-sized cyclic ethers has been achieved by means of nucleophilic substitution of the corresponding lactone-derived thioacetals and their sulfone counterparts. Nucleophilic substitution of medium-sized lactone-derived thioacetals could be achieved efficiently either by (i) activation with NIS/TMSOTf in the presence of allyltrimethylsilane or TMSCN or by (ii) oxidation to the corresponding sulfones followed by treatment with an appropriate organometallic species such as divinylzinc or dimethyl(2-phenylethynyl)aluminum. Interestingly, the stereochemical consequence was found to be largely dependent on the local structure of substrates. In some cases, the gauche steric interaction developed in the transition state was considered to be responsible for the observed diastereoselectivity. The present method enables an efficient synthesis of a variety of α,α′-substituted seven- to nine-membered cyclic ethers from readily accessible lactone precursors.

Expedient synthesis of complex γ-butyrolactones from 5-(1-arylalkylidene) meldrums acids via sequential conjugate alkynylation/Ag(I)-catalyzed lactonization

The conjugate alkynylation of alkylidene Meldrums acids with alkynylalanes and alkynyl Grignards allows for the formation of propargylic all-carbon quaternary stereocenters in high yields. Ag2CO3-catalyzed intramolecular cyclization

Synthesis of N,N-disubstituted 3-amino-1,4-diynes and 3-amino-1-ynes by addition of alkynyldimethylaluminum reagents to N,N-disubstituted formamides and N,O-acetals

A wide range of alkynyldimethylaluminum reagents, which were derived from terminal alkynes and trimethylaluminum, underwent a double addition to N,N-disubstituted formamides and their acetals to provide the corresponding N,N-disubstituted 3-amino-1,4-diynes in moderate to excellent yields. Also, these reagents smoothly underwent the addition to N,O-acetals to give the corresponding N,N-disubstituted 3-amino-1-ynes in excellent yields.