74646-37-0

Upstream product

• 112-31-2 caprinaldehyde 
• 106-96-7 propargyl bromide 
• 693-54-9 Decan-2-one 
• 624-65-7 2-propynyl chloride 
• 107820-22-4 ethyl prop-2-yn-1-yl carbonate 
• 945489-10-1 C₁₃H₂₅BrO 
• 138895-00-8 Allenyltetrabutylstiborane 

Relevant academic research and scientific papers

Gold-Catalyzed Tandem Oxidative Coupling Reaction between β-Ketoallenes and Electron-Rich Arenes to 2-Furylmethylarenes

A tandem oxidative coupling reaction of β-ketoallenes and arenes was developed, which leads to the formation of 2-furylmethylarenes using AuCl3 and phenyliodine diacetate. The AuIII salt catalyzed the cyclization of β-ketoallenes to form a 2-furylmethyl gold intermediate, and the subsequent C-H functionalization of arenes proceeded smoothly. During the oxidative coupling, nucleophilic additions occurred at the center and terminal carbon atoms of the allene moiety to form C-O and C-C bonds.

A practical procedure of propargylation of aldehydes

An operationally simple procedure of propargylation of aldehydes in moist solvent (distilled THF) has been developed through direct addition of propargyl bromide to aldehyde substrates mediated with low valent iron or tin. The metals were spontaneously pr

Highly selective barbier-type propargylations and allenylations catalyzed by titanocene(III)

The alkyne functional group is found in many bioactive natural products and is the key to many important chemical transformations developed over recent years. Moreover, allenes have recently gained relevance as versatile reagents in organic synthesis. Mild, catalytic methods to enable the selective introduction of either alkyne or allene motifs into organic molecules are very valuable but, as yet, quite scarce. We describe an extremely mild and selective method for either the propargylation or allenylation of carbonyl compounds catalyzed by the abundant, safe, and inexpensive metal titanium. These reactions can selectively provide homopropargylic alcohols from aldehydes and ketones or α-hydroxy-allenes from aldehydes. The mechanisms involved were also investigated. Copyright

Titanium/palladium-mediated regioselective propargylation of ketones using propargylic carbonates as pronucleophiles

An efficient protocol for the synthesis of homopropargylic alcohols using propargylic carbonates as pronucleophiles is reported. The reaction is based on a combination of transition metal (palladium) and radical chemistry (titanium). The reaction takes pl

Efficient propargylation of aldehydes and ketones catalyzed by titanocene(III)

We describe a novel method for the propargylation of a wide range of aldehydes and ketones catalyzed by titanocene(III) complexes under mild reaction conditions and compatible with many functional groups. Homopropargylic alcohols are obtained as the sole products even when ketones are used as starting materials, which is unusual in Barbier-type propargylations.

Preference of 4-exo ring closure in copper-catalyzed intramolecular coupling of vinyl bromides with alcohols

The copper-catalyzed intramolecular O-vinylation of γ-bromohomoallylic alcohols was investigated. With 10 mol % of CuI as the catalyst and 20 mol % of 1,10-phenanthroline as the ligand, the reactions of 3-bromo-3-buten-1-ols in refluxing CH3CN

Tetrabutylammonium fluoride-induced dehydrobromination of vinyl bromides to terminal acetylenes

Tetrabutylammonium fluoride (TBAF) was found to be a mild and efficient base for the dehydrobromination of vinyl bromides. Treatment of various 2-bromo-1-alkenes with TBAF·3H2O in DMF yielded terminal acetylenes in high yields without undue regard to the presence of water.

Gallium-mediated highly regioselective reaction of allyl-type bromide and propargyl-type bromide with aldehyde

In the presence of potassium iodide and lithium chloride, the one-pot reaction of gallium powder, allyl-type bromide and aldehyde shows very high selectivity favoring α-adducts. Under the same condition, the reaction of propargylic bromide with aldehyde e

On pentaorganylstiborane. III. Regio- and diastereoselective additions of acetylenic and allenic organoantimony compounds to aldehydes

The reaction of propargyl bromide (4a) with tributylstibine gave allenyltributylstibonium bromide (5), and its corresponding pentaorganylstiborane reacted with aldehyde to give homopropargylic alcohol (10a) exclusively in good yield.However, the reaction

Selective Synthesis of Allenic and Acetylenic Derivatives via Pentaorganylstiboranes

Allenyltetrabutylstiborane (3), formed from allenyltributylstibonium bromide (2) and butylmagnesium bromide, reacted with aldehydes to give homopropargylic alcohols (4) exclusively in excellent yields, while 2-butynyltetrabutylstiborane (6), formed from 2