67448-60-6

Upstream product

• 129217-85-2 trimethyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane 
• 98-86-2 acetophenone 
• 1196787-44-6 C₁₀H₂₀BNO₂Si 
• 43019-55-2 (3-methoxy-1-propyn-1-yl)trimethylsilane 
• 38002-45-8 3-bromo-1-(trimethylsilyl)-1-propyne 
• 1066-54-2 trimethylsilylacetylene 
• 75-11-6 diiodomethane 
• 143798-87-2 3-trimethylsilylprop-2-ynyldiisobutyltelluronium bromide 

Downstream Products

• 6712-35-2 2-phenylpent-4-yn-2-ol 

Relevant academic research and scientific papers

Regioselective propargylation of carbonyl compounds with (3-bromo-prop-1-ynyl)trimethylsilane promoted by reactive barium

A Barbier-type propargylation of aldehydes with (3-bromoprop-1-ynyl) trimethylsilane has been achieved using reactive barium as a low-valent metal in THF. This process is effective also for obtaining the desired homopropargylic alcohols in high yields fro

Copper-catalyst-controlled site-selective allenylation of ketones and aldehydes with propargyl boronates

A practical and highly site-selective copper-PhBPE-catalyst-controlled allenylation with propargyl boronates has been developed. The methodology has shown to be tolerant of diverse ketones and aldehydes providing the allenyl adducts in high selectivity. T

Zinc catalyzed and mediated propargylations with propargyl boronates

Chemical Equation Presented The utility of allenyl and propargyl boronates for the propargylation of aldehydes and ketones mediated by zinc is presented. The reaction is catalytic in zinc with allenyl or propargyl borolanes. The propargylation with crystalline and air-stable propargyl diethanolamine boronates was also achieved. A catalytic cycle is proposed, and preliminary mechanistic studies are discussed.

Regioselective addition reactions of propargyl bromides to carbonyl compounds with gallium catalyzed by indium

Reactions of organogallium reagents generated from propargyl bromides having substituents at the γ-position and gallium in the presence of 5 mol % of indium with aldehydes and ketones selectively produced homoallenyl alcohols in good to excellent yields.

Gallium-Mediated Highly Regioselective Reactions of Trimethylallylpropargyl Bromide and Trimethylsilylallyl Bromide with Carbonyl Compounds

One-pot reactions of gallium powder, trimethylsilylpropargyl bromide, aldehydes or ketones in the presence of KI and LiCl show very high acetylenic selectivity and under the same conditions, trimethylsilylallyl bromide also exhibits very high selectivity

Selective Mono- and Polymethylene Homologations of Copper Reagents Using (Iodomethyl)zinc Iodide

A wide range of unsaturated aryl-, alkenyl-, alkynylcopper compounds can be selectively homologated by a methylene unit using (iodomethyl)zinc iodide or bis(iodomethyl)zinc.These reactions allow the generation of mixed allylic zinc-copper compounds which can be efficiently trapped with carbonyl compounds.An application to a general preparation of functionalized α-methylene-γ-butyrolactones is described.The homologation of alkynylcoppers with (iodomethyl)zinc iodide allows a one-pot preparation of propargylic copper reagents which in the presence of a carbonyl compound provide various homopropargylic alcohols in excellent yields.In the absence of an electrophile, a clean quadruple methylene homologation of alkynylcoppers occurs to furnish dienic copper reagents.The homologation of other types of copper reagents is also possible, and carbanions at the α-position to amines as well as homoenolates of aldehydes or ketones can also be prepared by this method.

Reactions of Carbonyl Compounds with diisobutyltelluronium Bromide Mediated by Different Strong Bases: Highly Regioselective Synthesis of (Trimethylsilyl)propargyl Alcohol and Highly Stereoselective Synthesis of cis-(Trimethylsilyl)alkynyl Epoxides

diisobutyltelluronium bromide (1), after being treated with alkyl- or aryllithium reagent, undergoes a lithium-tellurium exchange reaction via an unstable transient tetraorganyltellurium intermediate, and the in situ generated lithium species react with carbonyl compounds to give (trimethylsilyl)propargyl alcohols 2 in high yields with high regioselectivity.However, when the telluronium salt 1 was treated with nonnucleophilic bases such as LDA or lithium 2,2,6,6-tetramethylpiperidide, the moderately stabilized silylated telluronium ylide formed.The silylated telluronium ylide reacted with carbonyl compounds to afford (trimethylsilyl)alkynyl epoxides 11 in good to excellent yields with high cis stereoselectivity.

Selective multiple methylene insertion reactions mediated by iodomethylzine iodide: Mechanistic considerations and synthetic applications

The reaction of alkynylcoppers 1 with an excess of iodomethylzinc iodide selectively furnishes the quadruple methylene insertion copper organometallics 2 in fair to good yields. The mechanism of the reaction has been investigated and postulated intermediates such as 4 or 8 have been trapped with electrophiles like aldehydes or ketones in excellent yields. A new in situ preparation of propargylic copper derivatives 4 starting from readily available alkynylcopper compounds has been developed leading to homopropargylic alcohols in 80-95% yield.