146491-85-2

Upstream product

• 124-13-0 Octanal 
• 932-88-7 1-iodo-2-phenylethyne 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 536-74-3 phenylacetylene 

Downstream Products

• 100905-25-7 1-phenyldec-1-yn-3-one 

Relevant academic research and scientific papers

Cascade and Effective Syntheses of Functionalized Tellurophenes

A one-pot and transition-metal-catalyst-free synthetic strategy to construct functionalized tellurophenes has been developed. Substituted 1,1-dibromo-1-en-3-ynes are smoothly converted to tellurophenes with telluride salts in high yield via a series of cascade reactions through reductive debromination, hydrotelluration, nucleophilic cyclization, and aromatization. Close inspection of the results clearly showed that the reactivity of in situ prepared telluride salts are significantly influenced by the polarity of the solvent system and the electronic nature of the substituent on the enyne substrate. This method reports the first direct synthesis of 3-aryltellurophenes in high yields at room temperature. This novel reaction strategy is also found to be a promising synthetic method for multisubstituted tellurophenes and selenophenes.

Catalytic asymmetric enyne addition to aldehdyes and Rh(I)-catalyzed stereoselective domino Pauson-Khand/[4 + 2] cycloaddition

The 1,1′-bi-2-naphthol-ZnEt2-Ti(OiPr) 4-Cy2NH system is found to catalyze the 1,3-enyne addition to aliphatic aldehydes as well as other aldehydes at room temperature with 75-96% yield and 82-97% ee. This system is also broadly applicable for the highly enantioselective reaction of other alkyl-, aryl-, and silylalkynes with structurally diverse aldehydes. The propargylic alcohols prepared from the catalytic asymmetric enyne addition to aliphatic aldehydes are used to prepare a series of optically active trienynes. In the presence of a catalytic amount of [RhCl(CO)2]2 and 1 atm of CO, the optically active trienynes undergo highly stereoselective domino Pauson-Khand/[4 + 2] cycloaddition to generate optically active multicyclic products. The Rh(I) catalyst is also found to catalyze the coupling of a diyne with CO followed by [4 + 2] cycloaddition to generate an optically active multicyclic product. These transformations are potentially useful for the asymmetric synthesis of polyquinanes containing a quaternary chiral carbon center.

Chiral macrocycle-catalyzed highly enantioselective phenylacetylene addition to aliphatic and vinyl aldehydes

(Chemical Equation Presented) The 1,1′-binaphthyl macrocycle (S)-2 is found to be an excellent catalyst for the alkyne addition to aldehydes. In the presence of (S)-2 (20 mol %) and Me2Zn (2 equiv) in THF at room temperature, the addition of ph

Me2Zn-mediated addition of acetylenes to aldehydes and ketones

Contrary to expectations, commercially available 2 M Me2Zn in toluene is able to promote the addition of phenylacetylene to aldehydes and ketones. This reactivity is determined by a new, unprecedented mechanism, which involves activation of the zinc reagent via coordination with carbonyl substrates that behave "ligand like". Broad scope, high tolerance to functional groups, and a simple procedure make this new method highly interesting for the synthetic chemist.

3,3′-Functionalized octahydro-BINOL: A facile synthesis and its high enantioselectivity in the alkyne addition to aldehydes

A facile synthesis of an enantiomerically pure 3,3′- bismorpholinylmethyl H8-BINOL ligand has been developed. This compound in combination with Et2Zn and Ti(OiPr) 4 is found to catalyze the highly enantioselecti

Indium-mediated carbonyl alkynylation

Indium mediates a Barbier-type reaction between alkynyl halides and aldehydes or ketones to give secondary or tertiary propargyl alcohols. Secondary alcohols can be oxidised in situ according an Oppenauer process.

Highly enantioselective phenylacetylene additions to both aliphatic and aromatic aldehydes.

The readily available and inexpensive BINOL in combination with Ti(O(i)Pr)(4) is found to catalyze the reaction of an alkynylzinc reagent with various types of aldehydes including aliphatic aldehydes, aromatic aldehydes, and other alpha,beta-unsaturated a

TBAHF2 and TBAH2F3 as Activating Agents of Organosilanes

The fluoride reagents, TBAH2F3 and TBAHF2 (TBA: tetrabutylammonium), are found to catalyze the reactions of hexamethyldisilane with 1,3-dienes, aliphatic aldehydes, and aromatic aldehydes to give 1,4-disilyl-2-butenes, α-silyl alcohols and pinacols, respectively. Using an equimolar amount of TBAHF2 and disilanes, reduction of carbonyl compounds occurs in place of the silyl group addition.

Direct Formation of Reactive Alkynyltrichlorotins from 1-Alkynes, SnCl4, and Bu3N. A Mild Alkynylation Reagent of Aldehydes, Acetals, and Enones

A reagent system of 1-alkyne, SnCl4, and Bu3N alkynylates aldehydes, acetals,and enones under mild reaction conditions giving acetylenic alcohols, acetylenic ethers, and acetylenic ketones, respectively, in high yields.Alkynyltrichlorotins are shown to be