69726-39-2

Upstream product

• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 93-08-3 methyl 2-naphthyl ketone 
• 108-86-1 bromobenzene 
• 13577-85-0 N,N-dimethyl-2-naphthylcarboxamide 
• 75-16-1 methylmagnesium bromide 
• 3262-89-3 triphenylboroxine 
• 98-80-6 phenylboronic acid 
• 7228-47-9 2-(2-naphthyl)ethanol 
• 100-58-3 phenylmagnesium bromide 
• 21473-01-8 2-naphthalenylmagnesium bromide 
• 98-86-2 acetophenone 

Downstream Products

• 28358-66-9 1-(2-naphthyl)styrene 

Relevant academic research and scientific papers

Iterative addition of carbon nucleophiles toN,N-dialkyl carboxamides for synthesis of α-tertiary amines

A protocol for the synthesis of α-tertiary amines was developed by iterative addition of carbon nucleophiles toN,N-dialkyl carboxamides. Nucleophilic 1,2-addition of organolithium reagents to carboxamides forms anionic tetrahedral carbinolamine (hemiaminal) intermediates, which are subsequently treated with bromotrimethylsilane (Me3SiBr) followed by organomagnesium (Grignard) reagents, organolithium reagents or tetrabutylammonium cyanide, affording α-tertiary amines. Employment of (trimethylsilyl)methylmagnesium bromide as the 2ndnucleophile allowed for aza-Peterson olefination of the resulting α-tertiary (trimethylsilyl)methylamines with acidic work-up, resulting in the formation of 1,1-diarylethylenes.

Bulky N-Heterocyclic-Carbene-Coordinated Palladium Catalysts for 1,2-Addition of Arylboron Compounds to Carbonyl Compounds

The synthesis of primary, secondary, and tertiary alcohols by the 1,2-addition of arylboronic acids or boronates to carbonyl compounds, including unactivated ketones, using novel bulky yet flexible N-heterocyclic carbene (NHC)-coordinated 2,6-di(pentan-3-yl)aniline (IPent)-based cyclometallated palladium complexes (CYPs) as catalysts is reported. The PhS-IPent-CYP-catalyzed reactions are efficient at low catalyst loadings (0.02–0.3 mol% Pd), and the exceptional catalytic activity for 1,2-addition is attributed to the steric bulk of the NHC ligand. These reactions can yield a wide range of functionalized benzylic alcohols that are difficult to synthesize by classical protocols using highly active organomagnesium or lithium reagents.

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.

Halogenation of 1,1-diarylethylenes by N-halosuccinimides

An efficient method for the preparation of 2,2-diarylvinyl halides from the corresponding 1,1-diarylethylenes has been developed. N-Halosuccinimides (N-bromosuccinimide or N-chlorosuccinimide) were used as the halogenation reagents. The practicability of this method is highlighted by its simple operation, broad substrate scope and capability for large-scale reaction.

Asymmetric Direct 1,2-Addition of Aryl Grignard Reagents to Aryl Alkyl Ketones

The enantioselective addition of Grignard reagents to ketones was promoted by a BINOL derivative bearing alkyl chains at the 3,3′-positions. This is the first asymmetric direct aryl Grignard addition to ketones reported to date. A variety of tertiary diaryl alcohols could be obtained in high yields and enantioselectivities without using any other metal source.

Catalytic Enantioselective Addition of Aryl Grignard Reagents to Ketones

We report a catalytic system for the challenging enantioselective addition of aryl Grignard reagents to ketones. Using a simple, one-pot procedure under mild conditions, a wide range of aromatic ketones are converted into diaryl alcohols in good yields and with good enantioselectivities. The catalytic enantioselective addition of aryl Grignard reagents to ketones is now possible. Using a readily available Ar-BINMOL ligand and titanium(IV) isopropoxide in a simple, one-pot procedure under mild conditions, a wide range of aromatic ketones are converted into diaryl alcohols in good yields and with good enantioselectivities.

Rhodium(I)/diene-catalyzed addition reactions of arylborons with ketones

Rh(I)/diene-catalyzed addition reactions of arylboroxines/arylboronic acids with unactivated ketones to form tertiary alcohols in good to excellent yields are described. By using C2-symmetric (3aR,6aR)-3,6-diaryl-1,3a,4,6a- tetrahydropentalenes as ligands, the asymmetric version of such an addition reaction, with up to 68% ee, was also realized.

Ni-catalysed, domino synthesis of tertiary alcohols from secondary alcohols

The use of in situ generated (NHC)-Ni catalytic species (NHC = N-heterocyclic carbene) allows for the synthesis, in short reaction times, of a variety of tertiary alcohols from secondary alcohols through a domino oxidation-addition protocol.

Synthesis and application of 2,6-bis(trifluoromethyl)-4-pyridyl phosphanes: The most electron-poor aryl phosphanes with moderate bulkiness

The poor will be rich: BFPy phosphanes (see scheme) mimic the electronic and steric characters of P(C6F5)3 and PPh 3, respectively. These novel ligands showed a large ligand acceleration effect on Stille coupling, the Rh-catalyzed 1,2-addition of aryl boronic acid to unactivated ketones and the asymmetric arylation of N-tosylimine using phenylboronic acid. Copyright

Controlled alcohol-carbonyl interconversion by nickel catalysis

All in one pot: A general synthetic platform allows the interconversion of alcohols and carbonyl compounds in a predictable and controlled fashion in one pot. Under the action of a Ni catalyst, PhCl, CsF, and arylboronates, several multistep alcohol-carbonyl interconversions have been achieved with good overall efficiency (see scheme). A one-pot nickel-catalyzed synthesis of flumecinol (a hepatic microsomal enzyme inducer) has also been demonstrated. Copyright