73222-65-8

Upstream product

• 24808-74-0 (E)-(3-methoxybut-1-en-1-yl)benzene 
• 762-72-1 allyl-trimethyl-silane 
• 112528-83-3 trans-1-Phenyl-3-(tetrahydropyran-2-yloxy)-1-butene 
• 112528-82-2 ((E)-3-Methoxymethoxy-but-1-enyl)-benzene 
• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 14371-10-9 (E)-3-phenylpropenal 
• 75-16-1 methylmagnesium bromide 
• 106-95-6 allyl bromide 
• 2622-05-1 allylmagnesium bromide 
• 52755-38-1 1-phenyl-2-buten-1-ol 
• 166021-49-4 (+/-)-(E)-3-benzyloxy-1-phenyl-1-butene 
• 52755-39-2 (2E)-1-phenylbut-2-en-1-ol 
• 17488-65-2 4-phenylbut-3-en-2-ol 
• 53317-08-1 9-allyl-9-bora-bicyclo[3.3.1]nonane 

Relevant academic research and scientific papers

Rhenium complex-catalyzed carbon-carbon formation of alcohols and organosilicon compounds

The coupling reactions of allylic and benzylic alcohols and allyltrimethylsilane are efficiently catalyzed by a rhenium complex to give the corresponding 1,5-dienes and alkenes in moderate to good yields. Similarly, alcohols were coupled with ketene silyl acetals to form the corresponding esters.

Chemoselective and direct functionalization of methyl benzyl ethers and unsymmetrical dibenzyl ethers by using iron trichloride

Methyl and benzyl ethers are widely utilized as protected alcohols due to their chemical stability, such as the low reactivity of the methoxy and benzyloxy groups as leaving groups under nucleophilic conditions. We have established the direct azidation of chemically stable methyl and benzyl ethers derived from secondary and tertiary benzyl alcohols. The present azidation chemoselectively proceeds at the secondary or tertiary benzylic positions of methyl benzyl ethers or unsymmetrical dibenzyl ethers and is also applicable to direct allylation, alkynylation, and cyanation reactions, as well as the azidation. The present methodologies provide not only a novel chemoselectivity but also the advantage of shortened synthetic steps, due to the direct process without the deprotection of the methyl and benzyl ethers. Ethers exchanged: Methyl and benzyl ethers are chemically stable and generally tolerant under nucleophilic substitution conditions. Iron-catalyzed direct functionalizations (e.g., azidation, allylation, alkynylation, and cyanation) of methyl and benzyl ethers derived from secondary and tertiary benzyl alcohols were established with excellent regioselectivities (see scheme; PG: protecting group; Bn: benzyl; Nu: nucleophile; TMS: trimethylsilyl). Copyright

High-yielding and rapid carbon-carbon bond formation from alcohols: Allylation by means of TiCl4

TiCl4 efficiently promotes high yield (80-99%) replacement of OH in tertiary, benzylic, and allylic alcohols, and even nonactivated secondary alcohols, by an allyl group. The reaction usually proceeds within minutes at room temperature. Georg Thieme Verlag Stuttgart. New York.

Fluorinated alcohols as promoters for the metal-free direct substitution reaction of allylic alcohols with nitrogenated, silylated, and carbon nucleophiles

The direct allylic substitution reaction using allylic alcohols in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) and 2,2,2-trifluoroethanol (TFE) as reaction media is described. The developed procedure is simple, works under mild conditions (rt, 50 and 70 °C), and proves to be very general, since different nitrogenated nucleophiles and carbon nucleophiles can be used achieving high yields, especially when HFIP is employed as solvent and aromatic allylic alcohols are the substrates. Thus, sulfonamides, carbamates, carboxamides, and amines can be successfully employed as nitrogen-based nucleophiles. Likewise, silylated nucleophiles such as trimethylsilylazide, allyltrimethylsilane, trimethylsilane, and trimethylsilylphenylacetylene give the corresponding allylic substitution products in high yields. Good results for the Friedel-Crafts adducts are also achieved with aromatic compounds (phenol, anisole, indole, and anilines) as nucleophiles. Particularly interesting are the results obtained with electron-rich anilines, which can behave as nitrogenated or carbon nucleophiles depending on their electronic properties and the solvent employed. In addition, 1,3-dicarbonyl compounds (acetylacetone and Meldrum's acid) are also successfully employed as soft carbon nucleophiles. Studies for mechanism elucidation are also reported, pointing toward the existence of carbocationic intermediates and two working reaction pathways for the obtention of the allylic substitution product.

Indium(i)-catalyzed alkyl-allyl coupling between ethers and an allylborane

An efficient method for alkyl-allyl cross-coupling between ethers and a 9-BBN-derived allylborane catalyzed by indium(i) triflate has been developed. The allylborane proved to be essential to obtain the desired products in high yields. The reaction displayed good substrate scope including high functional group tolerance. The Royal Society of Chemistry 2011.

Bis(fluorosulfuryl)imide: A Bronsted acid catalyst for the coupling of allylic and benzylic alcohols with allyltrimethylsilane

The Bronsted acid HN(SO2F)2 catalyses the reaction of allylic and benzylic alcohols with allyltrimethylsilane to give the corresponding coupled products in good yields.

Direct construction of quaternary carbons from carbonyl compounds utilizing low-valent vanadium complexes

Direct geminal diallylation of a carbonyl compound with allyl bromide has been achieved in the presence of a low-valent vanadium complex and zinc. The diallylation has been found to proceed stepwise and the two allyl groups were introduced successively. By applying this method, one-pot synthesis of asymmetric quaternary carbons has been accomplished. As the first alkylating reagent a combination of allyl bromide and zinc, a Grignard reagent, or an alkyllithium can be used. The second one should be the combination of a low- valent vanadium(II) complex and allyl bromide, benzyl bromide, or propargyl bromide. Strong oxophilicity of the low-valent vanadium facilitated the deoxygenative allylation.

A Facile Synthesis of 1,5-Dienes and β,γ-Unsaturated Nitriles via Trityl Perchlorate-Catalyzed Allylation

In the presence of a catalytic amount of trityl perchlorate, secondary and tertiary allyl ethers smoothly react with allylsilanes and silyl cyanide to give the corresponding 1,5-dienes and β,γ-unsaturated nitriles, respectively, in good yields.

Stereochemistry of the Reaction of an Optically Active ?-Allylpalladium Complex with Nucleophiles

The stereochemistry of the reaction of ?-allylpalladium complexes with nucleophiles has been elucidated using optically active (-)-(1S,2R,3R)-di-μ-chloro-bis(1-methyl-3-phenyl-?-allyl)dipalladium(II); dimethyl sodiomalonate and dimethylamine attack a carbon atom of the ?-allyl ligand from the side opposite to the palladium (inversion), and phenyl and allyl Grignard reagents attack the ?-allyl carbon atom from the same side as the palladium (retention).