19332-07-1

Upstream product

• 2550-26-7 4-Phenyl-2-butanone 
• 3277-89-2 phenethylmagnesium bromide 
• 98-86-2 acetophenone 
• 19332-06-0 4-Anilino-2,4-diphenyl-butanol-⁽²⁾ 
• 100-58-3 phenylmagnesium bromide 
• 103-63-9 1-phenyl-2-bromoethane 
• 17376-04-4 2-phenethyl iodide 
• 1083-30-3 dihydrochalcone 
• 917-54-4 methyllithium 
• 112448-69-8 3-phenyl-1-(1H-pyrrol-1-yl)propan-1-one 
• 645-45-4 hydrocinnamic acid chloride 
• 122-78-1 phenylacetaldehyde 
• 29443-41-2 β-phenylethylidenehydrazine 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 

Downstream Products

• 78484-95-4 1-Methyl-1,3-diphenylpropylhydroperoxid 
• 95954-15-7 3-Methyl-1,3,5-triphenylpentan 
• 7614-93-9 1,3-diphenyl-1-butene 
• 1520-44-1 1,3-diphenylbutane 
• 78485-07-1 3,5-diphenyl-3-methyl-1,2-dioxolane 
• 78485-08-2 3,5-diphenyl-3-methyl-1,2-dioxolane 

Relevant academic research and scientific papers

Cu-catalyzed cross-coupling of benzylboronic esters and epoxides

A reaction between epoxides and benzylboronic acid pinacol esters is described. CuI was found to be an effective catalyst of this transformation upon activation of the benzylboronic ester with an alkyllithium reagent. The reaction was very efficient and a variety of substituted epoxides were found to be good substrates with good regioselectivity for substitution at the less substituted side of the epoxide. A reaction using an enantioenriched secondary benzylboronic ester was found to not be stereospecific.

Shuttle arylation by Rh(I) catalyzed reversible carbon–carbon bond activation of unstrained alcohols

The advent of transfer hydrogenation and borrowing hydrogen reactions paved the way to manipulate simple alcohols in previously unthinkable manners and circumvented the need for hydrogen gas. Analogously, transfer hydrocarbylation could greatly increase the versatility of tertiary alcohols. However, this reaction remains unexplored because of the challenges associated with the catalytic cleavage of unactivated C–C bonds. Herein, we report a rhodium(I)-catalyzed shuttle arylation cleaving the C(sp2)–C(sp3) bond in unstrained triaryl alcohols via a redox-neutral β-carbon elimination mechanism. A selective transfer hydrocarbylation of substituted (hetero)aryl groups from tertiary alcohols to ketones was realized, employing benign alcohols as latent C-nucleophiles. All preliminary mechanistic experiments support a reversible β-carbon elimination/migratory insertion mechanism. In a broader context, this novel reactivity offers a new platform for the manipulation of tertiary alcohols in catalysis.

α-C-H borylation of secondary alcohols: Via Ru/Fe relay catalysis: Building a platform for alcoholic C-H/C-O functionalizations

An unprecedented α-C-H borylation of secondary alcohols was successfully achieved and delivered various tertiary α-boryl alcohols via [Ru]/[Fe] relay catalysis. The dehydrogenation catalyst (Ru) and borylation catalyst (Fe) interacted to increase the chemoselectivity. By installing the "platform functional group" Bpin via this α-C-H borylation, several alcoholic α-C-H and C-O bond functionalizations were successfully achieved.

NHC-coordinated palladacycle catalyzed 1,2-addition of arylboronates to unactivated ketones

Palladium catalyzed intermolecular 1,2-addition of arylboronate to unactivated ketone was investigated. NHC-coordinated palladacycle 4c exhibited catalytic activity for the reactions and provided the corresponding tertiary alcohols and γ,γ-disubstituted γ-lactones in good to excellent yields.

Aldehydes as alkyl carbanion equivalents for additions to carbonyl compounds

Nucleophilic addition reactions of organometallic reagents to carbonyl compounds for carbon-carbon bond construction have played a pivotal role in modern chemistry. However, this reaction's reliance on petroleum-derived chemical feedstocks and a stoichiometric quantity of metal have prompted the development of many carbanion equivalents and catalytic metal alternatives. Here, we show that naturally occurring carbonyls can be used as latent alkyl carbanion equivalents for additions to carbonyl compounds, via reductive polarity reversal. Such 'umpolung' reactivity is facilitated by a ruthenium catalyst and diphosphine ligand under mild conditions, delivering synthetically valuable secondary and tertiary alcohols in up to 98% yield. The unique chemoselectivity exhibited by carbonyl-derived carbanion equivalents is demonstrated by their tolerance to protic reaction media and good functional group compatibility. Enantioenriched tertiary alcohols can also be accessed with the aid of chiral ligands, albeit with moderate stereocontrol. Such carbonyl-derived carbanion equivalents are anticipated to find broad utility in chemical bond formation.

Remarkably stable tetrahedral intermediates: Carbinols from nucleophilic additions to N-acylpyrroles

Sufficiently stable intermediates formed in the reaction of N-acylpyrroles (1) with hydride and Grignard reagents can undergo further synthetic transformations and chromatographic purification to enable the generation of pyrrolecarbinols 2 in 76-95% yields [Eq. (1)].

Samarium-mediated Barbier reaction of carbonyl compounds

Samarium metal in the presence of catalytic amounts of iodine was found to be effective for the Barbier reaction of carbonyl compounds.

The reactivity of the high-energy intermediates formed in the reactions of Group 13 metal atoms and aromatic alkenes

Group 13 metal atoms were reacted with aromatic alkenes in a specialized metal atom reactor known as a "rotating cryostat." The nature of the intermediates formed was deduced from a GC-MS study of their hydrolysis and deuterolysis products. The product studies suggest that 2-phenylaluminacyclopropane, cis- and trans-3,4-diphenylaluminacyclopentane, and cis- and trans- 2,4-diphenylaluminacyclopentane are formed when A1 atoms react with styrene, and 2-methyl-2-phenylaluminacyclopropane and 3,4-dimethyl-3,4-diphenylaluminacyclopentane are formed when A1 atoms react with a-methylstyrene. These findings are consistent with the radicals detected in the EPR spectroscopic studies of A1-alkene reaction mixtures prepared under similar conditions. Mechanisms for the formation of the organoaluminium intermediates are discussed. Analogous organogallium intermediates are formed when gallium atoms react with styrene. The reductive coupling of styrene did not occur when In and T1 atoms were used. Only trace quantities of phenylethane were detected in the hydrolyzed reaction mixture.

A Novel C-C Single-Bond Formation Accompanying C-O Bond Cleavage by Use of a Ketone, an Alkylating Reagent, and a Low-Valent Vanadium Complex in the Presence of a Catalytic Amount of Molecular Oxygen

A C-C single-bond-forming reaction from ketones with accompanying C-O bond cleavage mediated by a RMgBr or RLi-vanadium(II)-O2 system has been accomplished. Different from conventional reductive coupling reactions of ketones such as the McMurry coupling, the present method forms a C-C single (instead of a double) bond and yields a product that contains components derived from the ketone and the alkylating reagent in a one-pot reaction. Collaboration of both a low-valent vanadium(II) species and a higher-valent vanadium species produced from vanadium(II) and a catalytic amount of O2 effects the abstraction of the oxygen atom from a C-O bond.