22127-86-2

Usage

Synthesis Reference(s)

Tetrahedron Letters, 22, p. 1359, 1981 DOI: 10.1016/S0040-4039(01)90319-3

Upstream product

• 124-13-0 Octanal 
• 106-96-7 propargyl bromide 
• 53915-69-8 allenyltributylstannane 
• 624-65-7 2-propynyl chloride 

Downstream Products

• 104-67-6 5-heptyldihydro-2(3H)-furanone 

Relevant academic research and scientific papers

Catalytic propargylation of aldehydes with allenyltributylstannane by ytterbium triflate

The first ytterbium triflate [Yb(OTf)3]-catalyzed propargylation of various aldehydes with allenyltributylstannane to afford homopropargyl alcohols in good yields is described. The present result provides a versatile tool for preparation of an array of homopropargyl alcohols from the reaction of aldehydes with allenyltributylstannane; which are known to possess low reactivity.

Carbonyl propargylation or allenylation by 3-haloprop-1-yne with tin(n) halides and tetrabutylammonium halides

3-Bromoprop-1-yne causes carbonyl propargylation with tin(n) chloride and tetrabutylammonium bromide in water to produce 1-substituted but-3-yn-1-ols, while 3-chloroprop-1-yne causes carbonyl allenylation with tin(II) iodide and tetrabutylammonium iodide in 1,3-dimethylimidazolidin-2-one to produce 1-substituted buta-2,3-dien-1-ols.

Barbier-type allylation of carbonyl compounds and imines with metallic cadmium

Cadmium mediated allylation of a variety of carbonyl compounds and imines in a Cd/Bu4NBr/THF system afforded excellent yields of the corresponding homoallylic alcohols and amines under very mild reaction conditions.

Selective Propargylation of Carbonyl Compounds with Allenylstannane/Alkyllithium Mixed Reagents

1-Substituted allenyltrialkylstannanes readily undergo transmetalation with an alkyllithium to generate a tetraalkylstannane and an equilibrating mixture of the allenyl- and propargyllithium compounds.The organolithium derivatives react with a variety of aldehydes and ketones at low temperature to give, after aqueous workup, the regioisomeric acetylenic and allenic carbinols in high yields.The degree of the regioselection is highly sensitive to the steric and electronic properties of the carbonyl substrates.Excellent acetylene selectivities are obtainable by combination of the bulky reagents and substrates or by using acylsilanes as carbonyl components.The origin of the regioselectivity is discussed.

Indium in Organic Synthesis: Indium-Mediated Allylation of Carbonyl Compounds

Indium-mediated allylation of a variety of ketones and aldehydes afforded excellent yields of the corresponding homoallylic alcohols under very mild reaction conditions.

Cadmium metal-mediated allylation of carbonyl compounds

Metallic cadmium prompted Barbier-type coupling of carbonyl compounds and allylic halides.The reaction was regio-selective giving homoallylic alcohols coupled at the γ-position of allylic halides. α,β-Unsaturated carbonyl compounds underwent only 1,2-addi

SAMARIUM DIIODIDE AS COUPLING AGENT BETWEEN ALDEHYDES AND ORGANIC HALIDES FOR THE SYNTHESIS OF HOMOALLYLIC AND HOMOBENZYLIC ALCOHOLS

Many aliphatic aldehydes are transformed into secondary alcohols by reaction with allyl halides or benzylic halides in presence of SmI2

SYNTHESE D'ALCOHOLS α-ALLENIQUES PAR REACTION D'ORGANOCHROMIQUES PROPARGYLIQUES SUR LES ALDEHYDES ET LES CETONES

Propargylic bromides can be condensed with aldehydes and ketones in the presence of Hiyama's reagent (2CrCl3+LiAlH4 in THF) leading to α-allenic alcohols, to homopropargylic alcohols or to the mixture of both of them.The selectivity (or specificity) of this reaction depends on the substitution of the propargylic bromide, on the structure of the ketone, and on the presence of HMPT in the reaction mixture.In many cases, α- allenic alcohol has been specifically or very selectively obtained.The mechanism of the reaction and the influence of the various parameters are discussed.