144776-78-3

Upstream product

• 54315-33-2 3-acetoxy-1-octyne 
• 201230-82-2 carbon monoxide 
• 766-77-8 Dimethylphenylsilane 
• 629-05-0 n-octyne 
• 116067-40-4 (±)-methyl oct-1-yn-3-yl carbonate 
• 144776-72-7 1-(1-Ethynyl-hexyl)-piperidine 

Relevant academic research and scientific papers

Synthesis of α-silylmethyl-α,β-unsaturated imines by the rhodium-catalyzed silylimination of primary-alkyl-substituted terminal alkynes

In contrast to our previous report on the rhodium-catalyzed reaction of terminal alkynes with equimolar amounts of hydrosilanes and isocyanides leading to (E)- or (Z)-β-silyl-α,β-unsaturated imines A, the addition of an excess molar amount of hydrosilanes relative to isocyanides in the reaction of primary-alkyl-substituted terminal alkynes results in the production of α-silylmethyl-α,β-unsaturated imines B. Various isocyanides bearing tert-butyl and 1-adamantyl groups gave B with good product selectivity. Z isomers were formed stereoselectively in many cases. Regarding the mechanism for this reaction, when the hydrosilane was added to the reaction mixture in two portions, unsaturated imines A were initially formed, which then underwent double-bond isomerization, probably catalyzed by a Rh-H species, to give B.

Rhodium-catalyzed transformation of propargyl alcohol derivatives to 2-silylmethyl-2-alkenals

Propargyl-type alcohols (6) and the corresponding esters of carbonic acid (4) or acetic acid (5) react with two equivalents of Me2PhSiH in the presence of catalytic amounts of Rh4(CO)12 under CO pressure at 100°C to give 2

Rhodium catalyzed transformation of propargylamines to 2-silylmethyl-2-alkenals: Formal silylformylation of allenes

Propargylamines are effectively transformed to 2-dimethylphenylsilylmethyl-2-alkenals by the interaction of two equivalents of Me2PhSiH under silylformylation conditions catalyzed by Rh4(CO)12. The products are not obtained directly by silylformylation of the corresponding allenes.