52922-11-9

Upstream product

• 122-78-1 phenylacetaldehyde 
• 18293-99-7 Prenyltrimethylsilane 
• 101-41-7 benzeneacetic acid methyl ester 
• 96-09-3 styrene oxide 
• 870-63-3 prenyl bromide 
• 114067-34-4 (3-methyl-2-butenyl)trifluorosilane 

Relevant academic research and scientific papers

Tuning the reactivity of organotin(IV) by LiOH: Allylation and propargylation of epoxides via redox transmetalation

In presence of catalytic Pd(0) or Pt(II), a reagent combination of SnCl2-LiOH promotes the reaction of organic halides and epoxides in dichloromethane leading to the regioselective formation of corresponding homoallyl and homopropargyl alcohols in good yields. This 2-carbon extension strategy adds to the repertoire of Barbier reactions via metal salts and reinforces views on the enhanced reactivity of organotin having -OH pendant.

Indium(I)/CuFe2O4 Reagent for Allylation of Carbonyls and Epoxide Rearranged Carbonyls

Abstract: Indium(I)/CuFe2O4 reagent forcarbonyl allylation and epoxide rearranged carbonyl allylation is proposed forformation of homoallylic alcohols. The In(I) reagent in combination withcatalytic amount of CuFe2O4support in situ formation of nucleophilicallylic indium from allyl halide in THF medium. Nucleophilic allylic indiumspecies react with carbonyls to form homoallyl alcohols in good to excellentyields. Under the presented reaction conditions arylepoxides undergo smoothrearrangement into aldehydes that are also allylated with formation of homoallylalcohols. The process is highly efficient and tolerates different functionalgroups.

Indium triiodide catalyzed direct hydroallylation of esters

The InI3-catalyzed hydroallylation of esters by using hydroand allysilanes under mild conditions has been accomplished. Many significant groups such as alkenyl, alkynyl, cyano, and nitro ones survive under these conditions. This reaction system, provided routes to both homoallylic alcohols and ethers, in which either elimination of the alkoxy moiety or of the carbonyl oxygen atom could be freely selected by changing the substituents on the alkoxy moiety and on the hydrosilane. In addition, the hydroallylation of lactones took place without ring cleavage to produce the desired cyclic ethers in high yields.

Highly efficient water promoted allylation and propargylation of arylepoxides via rearrangement-carbonyl addition

A simple and highly efficient one-pot procedure for allylation and propargylation of arylepoxides has been developed. A combination of SnCl 2 and catalytic Pd(0) or Pd(II) promotes the reaction of organic halides and epoxides in DMSO with controlled water addition, leading to the regioselective formation of the corresponding homoallyl and homopropargyl alcohols in good yields.

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.

REGIOSPECIFIC AND HIGHLY STEREOSELECTIVE ALLYLATION OF ALDEHYDES WITH ALLYLTRIFLUOROSILANE ACTIVATED BY FLUORIDE IONS.

Allyltrifluorosilane/CsF systems form pentacoordinate allylsiliconates which undergo chemoselective, regiospecific and highly stereoselective allylation of aldehydes, presumably via six-membered cyclic transition states.