66775-59-5

Upstream product

• 75-24-1 trimethylaluminum 
• 536-74-3 phenylacetylene 

Downstream Products

• 16917-32-1 (E)-2-chloro-1-methyl-1-phenylethene 
• 19647-26-8 (Z)-β-bromo-α-methylstyrene 
• 16917-35-4 (E)-(1-bromoprop-1-en-2-yl)benzene 
• 68669-68-1 (3E)-4-phenyl-1-trimethylsilyl-3-penten-1-yne 
• 25650-53-7 1-<(E)-1-methyl-2-methylsulfanyl-1-ethenyl>benzene 
• 23261-37-2 1-[(E)-1-methyl-2-(phenylsulfanyl)ethenyl]benzene 

Relevant academic research and scientific papers

Stereo- and Regiocontrolled Methylboration of Terminal Alkynes

A scalable and operationally simple synthesis of trisubstituted alkenyl boronic esters has been achieved using a Zr-catalyzed carboalumination of terminal alkynes followed by in situ transmetalation with i-PrOBpin. The products are formed in good yields and with excellent regioselectivity and perfect stereoselectivity. The new procedure provides a significant improvement over the previously reported syntheses.

Rhodium-Catalyzed Asymmetric Synthesis of β-Branched Amides

A general asymmetric route for the one-step synthesis of chiral β-branched amides is reported through the highly enantioselective isomerization of allylamines, followed by enamine exchange, and subsequent oxidation. The enamine exchange allows for a rapid and modular synthesis of various amides, including challenging β-diaryl and β-cyclic.

Zirconocene Catalysis in Organoaluminum Synthesis of 1-Alkenyl Sulfones and Sulfides

The Cp2ZrCl2-catalyzed methylalumination of 1-alkynyl sulfones and 1-alkynyl sulfides with Me3Al, followed by deuterolysis or hydrolysis, affords the corresponding β,β-disubstituted 1-alkenyl sulfones and 1-alkenyl sulfides in high yields. S-Methyl methanethiosulfonate is shown to be a convenient and efficient sulfanylating agent for 1-alkenylaluminum derivatives.

Zirconium-Catalyzed Alkyne Carbo- and Cycloalumination Reactions in Stereoselective Preparation of 1-Alkenyl Selenides

The Cp 2 ZrCl 2 -catalyzed methylalumination and Cycloalumination of 1-alkynyl selenides followed by deuterolysis or hydrolysis affords corresponding (Z)-1-alkenyl selenides in high yields. Alternatively, (E)-1-alkenyl selenides were prepared by the reaction of 1-alkenylaluminums with organic diselenides in a one-pot procedure starting from the corresponding 1-alkynes, which provides a versatile tool for the preparation of stereo-defined unsaturated organic derivatives of selenium.

One-Pot Synthesis of 1-Alkenyl Sulfides from Alkynes and Organic Disulfides with the Use of Organoaluminums

Organic disulfides (dipropyl, dihexyl, or diphenyl disulfide) are convenient and efficient agents for the sulfanylation of 1-alkenylaluminum derivatives.

The efficient method for the preparation of alkenylsilanes from organoaluminums

Silyl esters of sulfonic acids are convenient and efficient silylating agents for β,β- and β-substituted 1-alkenylaluminums. The reaction proceeds at room temperature in CH2Cl2 or hexane for 18 h to give corresponding alkenylsilanes in high yield. At the same time, α,β-disubstituted and α,β,β-trisubstituted 1-alkenylaluminums were inert in the reaction under study. The reaction with aluminacyclopen-2-enes and aluminacyclopentanes takes place on the less sterically hindered reaction center. Using electron-donating solvents (diethyl ether, THF) inhibits the reaction. A new convenient procedure of silylation was developed, which consists in obtaining the silyl tosylate by the reaction of chlorosilanes with anhydrous sodium tosylate in toluene solution. The resulting reaction mixture was reacted with organoaluminum compounds without isolation of silyl tosylate.

Efficient halogenation of unsaturated organoaluminum compounds with sulfonyl halides

Alkenylalumanes prepared by carbo-or cycloalumination of substituted acetylenes reacted with an equivalent amount of sulfonyl halide (MsCl, TsCl, PhSO2Cl, MsBr) in methylene chloride or hexane at room temperature to produce alkenyl halides in high yields. Electron-donor solvents such as diethyl ether or tetrahydrofuran inhibited the halogenation process. β-Substituted vinylalumanes generated by hydroalumination of substituted acetylenes failed to react with sulfonyl halides.

Enantioselective synthesis of quaternary carbon stereogenic centers through copper-catalyzed conjugate additions of aryl- and alkylaluminum reagents to acyclic trisubstituted enones

Acyclic quaternary carbons by conjugate addition: The first examples of catalytic enantioselective conjugate additions of aryl and alkyl units that generate acyclic all-carbon quaternary stereogenic centers have been developed (see scheme). The requisite

IMPROVED METHOD FOR THE PREPARATION OF ENANTIOMERICALLY ENRICHED SECONDARY ALCOHOLS BY THE ADDITION OF ORGANOALUMINIUM REAGENTS TO CARBONYL COMPOUNDS

A process for converting a carbonyl group within a substrate to a chiral alcohol moiety comprising reacting the carbonyl containing substrate with an organoaluminium reagent in the presence of a Group 5-12 transition metal based catalyst which is complexed with a chiral ligand; novel chiral ligands and organoluminium reagents, a chiral ligand or organoaluminium reagent for use in the process.