31650-08-5

Upstream product

• 673-32-5 1-Phenylprop-1-yne 
• 75-77-4 chloro-trimethyl-silane 
• 29578-46-9 trimethyl(3-phenylprop-2-yn-1-yl)silane 
• 10147-11-2 propargyl benzene 
• 1066-54-2 trimethylsilylacetylene 
• 100-39-0 benzyl bromide 
• 31683-47-3 1-(trimethylsilyl)-3-phenylprop-1-yne 

Downstream Products

• 85332-32-7 (2-Ethoxy-4-methyl-1-phenylvinylidene-pentyl)-trimethyl-silane 
• 85332-34-9 (1-Butoxymethyl-3-phenyl-propa-1,2-dienyl)-trimethyl-silane 
• 85332-36-1 (2-Ethoxy-1-phenylvinylidene-pent-4-ynyl)-trimethyl-silane 
• 85332-35-0 (2-Ethoxy-1-phenylvinylidene-pent-4-enyl)-trimethyl-silane 
• 85332-33-8 [1-(Methoxy-phenyl-methyl)-3-phenyl-propa-1,2-dienyl]-trimethyl-silane 
• 31650-09-6 1,3-bis(trimethylsilyl)-3-phenyl-allene 
• 91118-79-5 ((Z)-1,3-Bis-trimethylsilanyl-allyl)-benzene 
• 85332-43-0 [(Z)-2-Ethoxy-1-((E)-styryl)-penta-1,4-dienyl]-trimethyl-silane 
• 85332-44-1 [(Z)-2-Ethoxy-1-((E)-styryl)-pent-1-en-4-ynyl]-trimethyl-silane 

Relevant academic research and scientific papers

Propargylsilanes as Reagents for Synergistic Gold(I)-Catalyzed Propargylation of Carbonyl Compounds: Isolation and Characterization of σ-Gold(I) Allenyl Intermediates

Reported herein is the isolation and characterization, for the first time, of a σ-gold allenyl complex as an intermediate in gold catalysis. This intermediate was captured during the study of a novel gold(I)-catalyzed propargylation of carbonyl compounds with propargylsilanes. Notably, the gold-catalyzed propargylation reaction, which proceeds with aldehydes and ketones, can be driven to the formation of either homopropargyl silyl ethers or the in situ synthesis of corresponding 2-silyl-4,5-dihydrofurans.

Organomagnesium-catalyzed isomerization of terminal alkynes to allenes and internal alkynes

Organomagnesium complexes 2 were synthesized from N,N-dialkylamineimine ligands 1 and dibenzylmagnesium by benzylation of the imine moiety. 3-Aryl-1-propynes reacted with 2 to form the corresponding tetraalkynyl complexes, which acted as catalysts for the transformation of these terminal alkynes into allenes and further to internal alkynes under mild conditions. To the best of our knowledge, this example is the first of an organomagnesium-catalyzed isomerization of alkynes. Notably, the reactions proceeded through temporally separated autotandem catalysis, thus allowing the isolation of the allene or internal alkyne species in good yields. Mechanistic experiments suggested that the catalytically active tetraalkynyl complexes consist of a tautomeric mixture of alkynyl-, allenyl-, and propargylmagnesium species.

BIS(TRMETHYLSILYL)-1,3 ALCYNES-1 : PREPARATION A PARTIR DE SILANES PROPARGYLIQUES ET APPLICATION A LA SYNTHESE DE SILANES ALLENIQUES α-FONCTIONNELS

1,3-bis(trimethylsilyl)-1-alkynes may be obtained from trimethylsilylpropargylsilanes by metallation with n-butyllithium following by reaction with trimethylsilylchloride ; these silanes easily react with acetals, in presence of titanium tetrachloride, to produce α-functional allenyltrimethylsilanes.