81435-42-9

Upstream product

• 3355-28-0 1-Bromo-2-butyne 
• 2043-61-0 cyclohexanecarbaldehyde 
• 3355-17-7 1-chloro-2-butyne 
• 61493-85-4 but-2-yn-1-yl methanesulfonate 
• 138895-02-0 2-Butynyltetrabutylstiborane 
• 503-17-3 dimethylacetylene 

Downstream Products

• 86951-67-9 (R*)-<(1S*)-(Methylidenecyclopropyl)>cyclohexylmethanol 
• 192068-93-2 Diazo-acetic acid 1-cyclohexyl-2-methyl-buta-2,3-dienyl ester 

Relevant academic research and scientific papers

Regioselective addition reactions of propargyl bromides to carbonyl compounds with gallium catalyzed by indium

Reactions of organogallium reagents generated from propargyl bromides having substituents at the γ-position and gallium in the presence of 5 mol % of indium with aldehydes and ketones selectively produced homoallenyl alcohols in good to excellent yields.

Carbonyl allenylations and propargylations by 3-chloro-1-propyne or 2-propynyl mesylates with tin(IV) chloride and tetrabutylammonium iodide

By the use of tin(IV) chloride and tetrabutylammonium iodide in dichloromethane, 3-chloro-1-propyne or 2-propynyl mesylate can be applied to allenylation and propargylation of aldehydes (carbonyl allenylation and propargylation) to produce a mixture of 1-

A highly atom efficient, solvent promoted addition of tetraallylic, tetraallenic, and tetrapropargylic stannanes to carbonyl compounds

Tetraallylic, tetraallenic, and tetrapropargylic stannanes (0.25 equiv) react with aldehydes in methanol to provide unsaturated alcohols in good to excellent yields (56-99%). These reactions proceed exclusively with allylic rearrangement for tetra(2-butenyl)tin 2b and tetra(1,2-butadienyl)-tin 16c and predominantly with allylic rearrangement for tetrapropadienyltin 16a and tetra(2-butynyl)tin 6e. Allylation reactions also proceeded smoothly with reactive ketones such as ethyl pyruvate (9a) and cyclohexanone (9b). The corresponding TFA-catalyzed reactions of dimethyl acetals 4d and 4e are regiospecific with allylic rearrangement.

Carbonyl propargylation by 1-substituted prop-2-ynyl mesylates and carbonyl allenylation by 3-substituted prop-2-ynyl mesylates with tin(II) iodide and tetrabutylammonium iodide

1-Substituted prop-2-ynyl mesylates cause propargylation of aldehydes with tin(II) iodide, tetrabutylammonium iodide and sodium iodide in 1,3-dimethylimidazolidin-2-one to produce 2-substituted but-3-yn-1-ols, while 3-substituted prop-2-ynyl mesylates cau

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

Solvent assisted addition of tetraallylic, tetraallenic and tetrapropargylic stannanes to aldehydes and acetals

Tetraallylic, tetraallenic and tetrapropargylic stannanes (0.25 eq) react with aldehydes in methanol to provide unsaturated alcohols. These reactions proceed exclusively with allylic rearrangement for tetra(2-butenyl)tin 2b and tetra(1,2-butadienyl)tin 5e and predominantly with allylic rearrangement for tetrapropadienyltin Sc and tetra(2-butynyl)tin 6e. The corresponding TFA catalysed reactions of dimethyl acetals with Sc and 6e are highly regioselective with allylic rearrangement.

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

Regio- and Stereocontrolled Synthesis of Allenic and Acetylenic Derivatives. Organotitanium and Boron Reagents

The propargyltitanium reagents derived from 1-alkylpropyne condensed with aldehydes to give α-allenyl alcohol regioselectively, while the allenyltitanium reagents generated from 1-alkyl-1-butyne derivatives gave threo-β-acetylenic alcohols with high regio- and stereoselectivities.The course of the reaction was determined by the substitution pattern of starting alkynes.The similar reactions of metallated 1,3-bis(trialkylsilyl)propyne or (trialkylsilyl)acetonitrile with aldehydes were also investigated.

Propargylic Titanium Reagents. Regio- and Stereocontrolled Synthesis of Allenic and Acetylenic Alcohols

The highly selective condensations of propargylic titanium reagents and aldehydes are described.