58824-56-9

Upstream product

• 3536-96-7 vinylmagnesium chloride 
• 1122-91-4 4-bromo-benzaldehyde 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 1826-67-1 vinyl magnesium bromide 
• 106-37-6 1.4-dibromobenzene 
• 107-02-8 acrolein 
• 104293-07-4 (E)-1-bromo-4-(3-chloroprop-1-en-1-yl)benzene 

Downstream Products

• 105515-33-1 (2E)-3-(4-bromophenyl)prop-2-en-1-ol 
• 1073277-36-7 α-vinyl-(4-bromo-phenyl)methanol 
• 1073277-37-8 (R)-(-)-1-acetoxy-1-(4-bromophenyl)-2-propylene 
• 1073277-21-0 (+/-)-1-(4'-bromophenyl)prop-2-en-1-yl tert-butyl carbonate 
• 10342-83-3 4'-Bromopropiophenone 
• 1044744-75-3 (E)-4-(3-(4-bromophenyl)allyl)-2,6-dimethylphenol 
• 1204403-30-4 1-(4-bromophenyl)allyl isopropyl carbonate 
• 33342-24-4 2-(4-bromophenyl)-5-methylfuran 
• 1234617-97-0 1-(4-bromophenyl)allyl benzoate 
• 1308888-05-2 (S,E)-5-(4-bromophenyl)-3-(nitromethyl)pent-4-enal 
• 1308888-14-3 (E)-5-(4-bromophenyl)pent-4-en-1-ol 
• 1308888-07-4 (E)-5-(4-bromophenyl)pent-4-enal 
• 1340481-60-8 1-(4-bromophenyl)-2-fluoropropan-1-one 

Relevant academic research and scientific papers

1,4-Diazabicyclo[2.2.2]octane-Promoted Aminotrifluoromethylthiolation of α,β-Unsaturated Carbonyl Compounds: N-Trifluoromethylthio-4-nitrophthalimide Acts as Both the Nitrogen and SCF3 Sources

A novel difunctionalization reaction is described. It uses N-trifluoromethylthio-4-nitrophthalimide as the reagent, which serves as both the nitrogen and SCF3 sources. In the presence of DABCO (1,4-diazabicyclo[2.2.2]octane), the nitrogen and SCF3 groups can be incorporated into α,β-unsaturated carbonyl compounds easily and give versatile β-amino ketones and esters in good yields. This difunctionalization reaction features mild reaction conditions, high atom-economy, and efficient access to α-SCF3 amino acids.

Nickel-Mediated Enantiospecific Silylation via Benzylic C-OMe Bond Cleavage

Benzylic stereocenters are found in bioactive and drug molecules, as enantiopure benzylic alcohols have been used to build such a stereogenic center, but are limited to the construction of a C-C bond. Silylation of alkyl alcohols has the potential to build bioactive molecules and building blocks; however, the development of such a process is challenging and unknown. Herein, we describe an unprecedented AgF-assisted nickel catalysis in the enantiospecific silylation of benzylic ethers.

Size-Exclusion Borane-Catalyzed Domino 1,3-Allylic/Reductive Ireland–Claisen Rearrangements: Impact of the Electronic and Structural Parameters on the 1,3-Allylic Shift Aptitude

The reductive Ireland–Claisen rearrangement through borane-mediated hydrosilylation is reported. The method employs a borane catalyst with a special structural design and affords access to synthetically relevant products with high diastereoselectivity. Depending on electronic and structural parameters, the reaction can be coupled with a 1,3-allylic shift, thus the valence isomer of the Ireland–Claisen product is formed.

Enantioselective addition of selenosulfonates to α,β-unsaturated ketones

An organo-catalyzed enantioselective addition of selenosulfonates to α,β-unsaturated ketones was developed for the first time. With a chiral squaramide as an efficient catalyst, the desired α-selenylated ketones were obtained in a good yields with high enantioselectivity up to 89% ee, and good results could be obtained on a gram scale. The products could also be efficiently transformed into useful building blocks with a propenylic stereocenter; the strategy presented in this study may find further applications in organic synthesis.

Grubbs cross-metathesis pathway for a scalable synthesis of γ-keto-α,β-unsaturated esters

A direct and scalable route to γ-keto-α,β-unsaturated esters, useful intermediates in medicinal chemistry and natural products synthesis, is reported. The key step involves the use of Grubbs' second-generation olefin metathesis catalyst for cross-metathes

Synthesis of (±)-amathaspiramide F and discovery of an unusual stereocontrolling element for the [2,3]-stevens rearrangement

A formal total synthesis of (±)-amathaspiramide F through a tandem palladium-catalyzed allylic amination/[2,3]-Stevens rearrangement is reported. The unexpected diastereoselectivity of the [2,3]-Stevens rearrangement was controlled by the substitution pat

A novel one-pot synthesis of secondary alcohols from esters

Alkylation or vinylation by using organometallic reagents after partial reduction of carboxylic esters with LDBBA gave secondary alcohols, also involving allyl alcohols, without any isolation of intermediates in good yield (54-78%).

Ruthenium-catalyzed synthesis of allylic alcohols: Boronic acid as a hydroxide source

Secondary allylic alcohols were synthesized from linear allylic halides or carbonates using a catalytic amount of a ruthenium complex in the presence of boronic acid. The effects of solvent, base, ruthenium precursor, and boronic acid were fully explored, and the scope of the reaction was extended to various sub-strates. We also describe a preliminary investigation towards an enantioselective process.

Pentamethylcyclopentadienyl ruthenium: an efficient catalyst for the redox isomerization of functionalized allylic alcohols into carbonyl compounds

The catalytic activity of the ruthenium(II) complex [RuCp*(CH3CN)3][PF6] 1 in the transposition of allylic alcohols into carbonyl compounds, in acetonitrile, is reported. This catalyst has proven to be able to catalyze the transformation of poorly reactive and/or functionalized substrates under smooth conditions.

Tandem oxidation/halogenation of aryl allylic alcohols under Moffatt-Swern conditions

(Chemical Equation Presented) Aryl allylic alcohols are converted to halogenated unsaturated ketones or allylic halides using excess Moffatt-Swern reagent. Electron-poor aromatic rings favor formation of the halogenated ketone, while electron-donating substituents in the ortho or para positions favor formation of the allylic halide. The oxidation/halogenation reaction performs well with both oxalyl chloride and oxalyl bromide, providing access to the corresponding chlorides or bromides, respectively.