75405-41-3

Upstream product

• 106-96-7 propargyl bromide 
• 768-33-2 phenyldimethylsilyl chloride 
• 624-65-7 2-propynyl chloride 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 

Downstream Products

• 120978-57-6 1-dimethylphenylsilyl-2-triphenylgermyl-1-propene 
• 120978-55-4 3-dimethylphenylsilyl-2-triphenylstannyl-1-propene 
• 120978-56-5 1-dimethylphenylsilyl-2-triphenylstannyl-1-propene 
• 1131688-23-7 C₁₈H₂₆O 
• 1131688-25-9 C₂₁H₃₀O 
• 1131688-24-8 C₂₁H₃₂O 
• 866408-99-3 (1R,2R)-2-[dimethyl(phenyl)silyl]-1-phenylbut-3-en-1-ol 
• 956430-54-9 (1S,2S)-2-[dimethyl(phenyl)silyl]-1-phenylbut-3-en-1-ol 

Relevant academic research and scientific papers

Stereoselective Syntheses of γ,δ-Bifunctionalized Homoallylic Alcohols and Ethers via Chemoselective Allyl Addition to Aldehydes

Stereoselective synthesis of γ,δ-bifunctionalized homoallylic alcohols and ethers via chemoselective allylation is reported. Pd-catalyzed 1,2-diboration of allenylsilane provided a novel 1,1,2-trifunctional allylation reagent. Allylboration of aldehydes w

Copper(I)-catalyzed regio- and chemoselective single and double addition of nucleophilic silicon to propargylic chlorides and phosphates

Copper(I)-catalyzed propargylic substitution of linear precursors with (Me2PhSi)2Zn predominantly yields the γ isomer independent of the propargylic leaving group. The thus formed allenylic silane reacts regioselectively with another equivalent of (Me2PhSi) 2Zn, yielding a bifunctional building block with allylic and vinylic silicon groups. The reaction rates of both steps are well-balanced for chloride (γ:α ≥ 99:1) where the propargylic displacement occurs quantitatively prior to the addition step. Substitutions of α-branched propargylic phosphates are also reported.

Copper(I)-catalyzed regioselective propargylic substitution involving Si-B bond activation

The silicon nucleophile generated by copper(I)-catalyzed Si-B bond activation allows several γ-selective propargylic substitutions. The regioselectivity (γ:α ratio) is strongly dependent on the propargylic leaving group. Chloride is superior to oxygen leaving groups in linear substrates (γ:α > 99:1), and it is only the phosphate group that also shows promising regiocontrol (γ:α = 90:10). That leaving group produces superb γ-selectivity (γ:α > 99:1) in α-branched propargylic systems, and enantioenriched substrates react with excellent central-to-axial chirality transfer.

Palladium(II)-catalyzed cycloisomerization of functionalized 1,5-hexadienes

Scope and limitations of the Pd(II)-catalyzed cycloisomerization of functionalized 1,5-hexadienes have been studied. In situ NMR experiments indicate a challenging competition between various reaction pathways. A careful balance between substrate structur

Regioselective allene synthesis and propargylations with propargyl diethanolamine boronates

"Chemical Equation Presented" The utility of propargyl diethanolamine boronates as reagents for the preparation of allenes and homopropargylic alcohols is presented. Protonolysis with TFA and electrophilic substitution with N-halosuccinimides proceeded wi

Selective mono- and di-allylation and allenylation of chlorosilanes using indium

Allyl and allenyl groups have been introduced into silicon systems by the allylation and allenylation of chlorosilanes using allyl bromide or propargyl bromide with indium. The allylation of chlorosilanes afforded a variety of aryl, aralkyl, and alkenyl substituted allylsilanes. By applying this method, the reactions of 1-bromo-3-methylbut-2-ene, 3-bromo-2-methylprop-1-ene and 3-bromobut-1-ene with chlorosilanes also proceed smoothly to give regioselectively allylic rearrangement products in good yields. Mediated by indium, dichlorosilanes (R2SiCl2) and trichlorosilanes (RSiCl3) can either afford monoallylated silanes or diallylated silanes depending on the amount of allyl bromide and indium used.

Silyl-cupration of a propargylsilane as a test for the reversibility of a metallo-metallation

Silyl-cupration of propargylsilanes is normal in giving mainly the product with a silyl group at the terminus and the copper atom in the centre. There is no evidence of the copper atom and the originally-resident silyl group undergoing a retro silyl-cupration to give an allenylsilane.