35342-69-9

Upstream product

• 6738-06-3 phenylethynylmagnesium bromide 
• 18925-10-5 allylzinc bromide 
• 536-74-3 phenylacetylene 
• 57501-29-8 4-chloro-4-phenyl-pent-1-ene 
• 134306-67-5 2-(2-hydroxy-2-phenyl-4-pentenylseleno)benzothiazole 
• 532-27-4 1-chloroacetophenone 
• 1730-25-2 allylmagnesium bromide 
• 134306-62-0 2-(2-phenyl-2-oxoethylseleno)benzothiazole 
• 107-05-1 3-chloroprop-1-ene 
• 762-72-1 allyl-trimethyl-silane 
• 24850-33-7 allyltributylstanane 
• 164073-53-4 4-phenyl-4-trimethylsiloxy-1-pentene 
• 556-56-9 allyl iodid 
• 3240-11-7 Phenylacetylene-d1 

Downstream Products

• 64-18-6 formic acid 
• 98-86-2 acetophenone 
• 65-85-0 benzoic acid 
• 144-62-7 oxalic acid 
• 346623-42-5 (2S)-2-methyl-4-phenyl-4-penten-1-ol 
• 346623-44-7 (2R)-2-methyl-4-phenyl-4-penten-1-ol 
• 1277169-54-6 dimethyl 2-allyl-2-phenylcyclopropane-1,1-dicarboxyl 
• 101999-42-2 (+/-)-2-phenyl-1,5-pentanediol 

Relevant academic research and scientific papers

Zn/[bmim]PF6-mediated Markovnikov allylation of unactivated terminal alkynes

A simple and highly regioselective method has been developed for the allylation of unactivated terminal alkynes with allyl bromide using Zn/[bmim]PF6 as an inexpensive, readily available and recyclable reagent system. High conversions and enhan

A convenient method for the generation of allylic dihaloboranes and diallyl(chloro)borane and their application in the allylboration of alkenes and acetylenes

A convenient approach to the highly reactive allylic dihaloboranes and diallyl(chloro)borane based on exchange reactions between BHal3 (Hal = Cl, Br) and allylic triorganoboranes (allyl, cinnamyl and 2- methylenecyclobutane derivatives) has bee

Indium-mediated regioselective Markovnikov allylation of unactivated terminal alkynes

Allylation of unactivated terminal alkynes by a simple treatment with allyl bromide and indium metal in THF at room temperature produces 1,4-dienes via regioselecttve Marknovnikov addition.

MIDA boronate allylation-synthesis of ibuprofen

MIDA boronates are among the most useful reagents for the Suzuki-Miyaura reaction. This chemistry typically generates new bonds between two aromatic rings, thereby restricting access to important areas of chemical space. Here we demonstrate the coupling of MIDA boronates to allylic electrophiles, including a new synthesis of the well-known COX inhibitor ibuprofen. This journal is

Silylium-Ion-Promoted (5+1) Cycloaddition of Aryl-Substituted Vinylcyclopropanes and Hydrosilanes Involving Aryl Migration

A transition-metal-free (5+1) cycloaddition of aryl-substituted vinylcyclopropanes (VCPs) and hydrosilanes to afford silacyclohexanes is reported. Catalytic amounts of the trityl cation initiate the reaction by hydride abstraction from the hydrosilane, and further progress of the reaction is maintained by self-regeneration of the silylium ions. The new reaction involves a [1,2] migration of an aryl group, eventually furnishing 4- rather than 3-aryl-substituted silacyclohexane derivatives as major products. Various control experiments and quantum-chemical calculations support a mechanistic picture where a silylium ion intramolecularly stabilized by a cyclopropane ring can either undergo a kinetically favored concerted [1,2] aryl migration/ring expansion or engage in a cyclopropane-to-cyclopropane rearrangement.

Selective Synthesis of Silacycles by Borane-Catalyzed Domino Hydrosilylation of Proximal Unsaturated Bonds: Tunable Approach to 1,n-Diols

The tris(pentafluorophenyl)boron-catalyzed domino hydrosilylation of substrates carrying unsaturated functionalities in a proximal arrangement is presented to produce silacycles. Excellent levels of efficiency and selectivity were achieved in the cyclization by the deliberate choice of the hydrosilane reagents. The key to successful cyclic hydrosilylation is the reactivity enhancement of the second intramolecular hydrosilylation by a proximity effect. Not only dienes but also enones, enynes, ynones and enimines readily afford medium-sized silacycles under convenient and mild conditions. The cyclization proceeds with acceptable diastereoselectivity mainly controlled by the conformational bias towards inducing additional stereogenic centers. The silacycles obtained from this reaction were converted to 1,n-diols or 1,n-amino alcohols upon oxidation, thus rendering the present cyclization a powerful tool for accessing synthetically valuable building blocks. (Figure presented.).

A novel ketone olefination via organozinc reagents in the presence of diphenyl phosphite

Carbonyl compounds react with organozinc reagents in the presence of diphenyl phosphite to give the corresponding olefins. A variety of 1,3-dienes and unsaturated esters were obtained in moderate to excellent yields under mild conditions. The Royal Society of Chemistry 2012.

Palladium-catalyzed allyl cross-coupling reactions with in situ generated organoindium reagents

Inter- and intramolecular palladium-catalyzed allyl cross-coupling reactions, using allylindium generated in situ from allyl halides and indium, is demonstrated. Allylindium compounds may be effective nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions. A variety of allyl halides, such as allyl iodide, allyl bromide, crotyl bromide, prenyl bromide, geranyl bromide, and 3-bromocyclohexene afforded the allylic cross-coupling products in good to excellent yields. Stereochemistry of the double bond is retained in the allylic cross-coupling reactions. Electrophilic cross-coupling partners, such as aryl and vinyl halides, dibromoolefin, alkynyl iodide, and aryl and vinyl triflates participate in these reactions. The presence of various substituents, such as n-butyl, ketal, acetyl, ethoxycarbonyl, nitrile, N-phenylamido, nitro, and chloride groups on the aromatic ring of electrophilic coupling partners showed little effect on the efficiency of the reactions. The present conditions work equally well for not only intermolecular but also intramolecular palladium-catalyzed cross-coupling reactions. These methods provide an efficient synthetic method for the introduction of an allyl group, which can be easily further functionalized to afford an sp2- and sp-hybridized carbon. The present method complements existing synthetic methods as a result of advantageous features such as easy preparation and handling, thermal stability, high reactivity and selectivity, operational simplicity, and low toxicity of allylindium reagents.

Regioselective synthesis of 1-bromo-1,4-dienes by free-radical-mediated bromoallylation of activated acetylenes

The free-radical-mediated bromoallylation of acetylenes proceeded efficiently in the presence of V-65 (2,2-azobis(2,4-dimethylvaleronitrile)) as the radical initiator. The regioselective reaction, which yields 1-bromo-2-substituted 1,4-dienes, is complementary to the Pd-catalyzed bromoallylation reaction previously reported by Kaneda. The products of the free-radical-mediated bromoallylation of acetylenes could be converted into a variety of substituted dienes by subsequent Pd-catalyzed reactions.

A novel and efficient method for the olefination of carbonyl compounds with Grignard reagents in the presence of diethyl phosphite

The widely available carbonyl compounds react with Grignard reagents in the presence of diethyl phosphite to give the corresponding olefins in good to excellent yields: A range of conjugated dienes, terminal olefins, multisubstituted-alkenes and conjugated enynes could be readily obtained by the method in mild conditions.