62692-40-4

Upstream product

• 513-31-5 2-bromoallyl bromide 
• 6921-34-2 benzylmagnesium chloride 
• 2550-26-7 4-Phenyl-2-butanone 
• 64884-77-1 4-methyl-N'-(4-phenylbutan-2-ylidene)benzenesulfonohydrazide 
• 100-44-7 benzyl chloride 
• 16520-62-0 4-Phenyl-1-butyne 
• 65674-14-8 1,2-dibromo-4-phenylbutane 
• 3112-88-7 Benzyl phenyl sulfone 
• 100-39-0 benzyl bromide 
• 62692-29-9 C₁₆H₁₅BrO₂S 

Downstream Products

• 115045-60-8 1-(3-butyl-3-butenyl)benzene 
• 1415610-31-9 (R)-3-((4,4,6-trimethyl-1,3,2-dioxaborato)methyl)-5-phenylpentanoic acid phenyl amide 
• 1391742-83-8 (R)-2-(4-phenylbutan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1391742-82-7 2-(4-phenylbut-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 904689-49-2 1,1,2-tribromo-2-(2-phenylethyl)cyclopropane 
• 115045-62-0 Trimethyl-((Z)-3-methylene-5-phenyl-pent-1-enyl)-silane 

Relevant academic research and scientific papers

Synthesis of functionalized cyclopropylboronic esters based on a 1,2-metallate rearrangement of cyclopropenylboronate

A procedure converting tribromocyclopropane to densely functionalized β-selenocyclopropylboronic ester using the 1,2-metallate rearrangement of a boron ate-complex has been developed. Treatment of an in situ-generated cyclopropenylboronic ester ate-complex with phenylselenenyl chloride triggered stereospecific rearrangement to produce functionalized cyclopropanes. DFT calculations for 1,2-metallate rearrangement suggested that the reaction proceeds through a seleniranium intermediate. This journal is

A catalytic allylic cation-induced intermolecular allylation-semipinacol rearrangement

A catalytic intermolecular semipinacol rearrangement induced by allylic carbocations has been realized. This tandem reaction is highly efficient under the catalysis of ZnBr2, generating a wide range of α-homoallyl substituted ketones which contain all-carbon quaternary centres in good to excellent yields (up to 98%) with moderate to high diastereoselectivities (up to >20?:?1). Synthetic application of this novel methodology in the construction of core structures of natural products is also reported.

Synthesis of Spirocyclic Ethers by Enantioselective Copper-Catalyzed Carboetherification of Alkenols

Spirocyclic ethers can be found in bioactive compounds. This copper-catalyzed enantioselective alkene carboetherification provides 5,5-, 5,6- and 6,6-spirocyclic products containing fully substituted chiral carbon centers with up to 99 % enantiomeric exce

Brook Rearrangement as Trigger for Carbene Generation: Synthesis of Stereodefined and Fully Substituted Cyclobutenes

Through a sequence that can be performed in a single vessel, involving regio- and diastereoselective copper-catalyzed carbomagnesiation of cyclopropenes, reaction with acylsilanes, and addition of THF as cosolvent, Brook rearrangement can be triggered to furnish a wide range of cyclobutenes with exceptional diastereoselectivity. Accordingly, stereodefined and highly substituted cyclobutenes with contiguous quaternary carbon centers can be synthesized easily and in high yield. The new strategy constitutes an unprecedented application of Brook rearrangement, one which involves the intermediacy of carbene species.

Regioselective Synthesis of Vinyl Halides, Vinyl Sulfones, and Alkynes: A Tandem Intermolecular Nucleophilic and Electrophilic Vinylation of Tosylhydrazones

A diazo species is trapped in an intermolecular fashion by two independent ion species in tandem at the carbene center to install an electrophile and a nucleophile on the same carbon. This metal-free concept, which is unprecedented, has been illustrated by regioselective synthesis of a variety of vinyl halides, vinyl sulfones, and alkyne derivatives. (Chemical Equation Presented).

γ-Selective directed catalytic asymmetric hydroboration of 1,1-disubstituted alkenes

Directed catalytic asymmetric hydroborations of 1,1-disubstituted alkenes afford γ-dioxaborato amides and esters in high enantiomeric purity (90-95% ee). The Royal Society of Chemistry 2012..

Iridium-catalyzed enantioselective hydrogenation of alkenylboronic esters

Choose the right ligand: An iridium complex derived from a phosphino-imidazoline ligand is a highly efficient catalyst for the asymmetric hydrogenation of terminal vinyl boronic esters (see scheme). On the other hand, trisubstituted alkenyl-boronates can

TBAF-promoted elimination of vicinal dibromides having an adjacent O-functional group: Syntheses of 2-bromoalk-1-enes and alkynes

Syntheses of 2-bromoalk-1-enes and alkynes were achieved in good yields by dehydrobromination of vicinal dibromides with tetrabutylammonium fluoride. Neighboring O-functional-group participation is important in determining elimination reactivity. Georg Thieme Verlag Stuttgart New York.

TBAF-promoted dehydrobrominations of vicinal dibromides having an adjacent O-functional group

Regioselective HBr elimination of vicinal dibromides having an adjacent oxygen functional group to give the corresponding 2-bromoalk-1-enes was controlled using 1.1 equivalents of TBAF. Two-step elimination to give the corresponding alkynes was controlled using 5.0 equivalents of TBAF. High yield and high selectivity require the presence of an oxygen functional group at the neighboring position of the elimination site.

Neighbouring-group influence on the ring opening of some 2-alkyl-1,1,2-tribromocyclopropanes under phase-transfer conditions

Several 2-alkyl-1,1,2-tribromocyclopropanes were treated with sodium hydroxide and ethanol under phase-transfer conditions. Ring opening gave mixtures of the corresponding acetylenic diethyl ketals and acetals. When the steric bulk of the alkyl substituent was increased acetal formation dominated, and in the case of 1,1,2-tribromo-2-(tert-butyl)cyclopropane, the acetal was formed as the only product. Springer-Verlag 2005.