72774-00-6

Upstream product

• 1201594-02-6 4-methoxynaphthalen-1-yl diethylcarbamate 
• 98-80-6 phenylboronic acid 
• 421555-84-2 C₁₆H₁₈O₄ 
• 1201594-33-3 C₁₃H₁₅NO₄S 
• 2216-69-5 1-Methoxynaphthalene 
• 5467-58-3 1-bromo-4-methoxynaphthalene 
• 62673-29-4 phenyl(diisobutyl)aluminium 
• 108-86-1 bromobenzene 
• 1072840-83-5 4-methoxynaphthalen-1-yl pivalate 
• 78250-37-0 1-Acetoxy-4-phenylnaphthalene 
• 36159-76-9 4-phenyl-1-naphthol 
• 108-94-1 cyclohexanone 
• 24821-54-3 1-methoxy-4-methylnaphthalene 
• 71-43-2 benzene 

Downstream Products

• 36159-76-9 4-phenyl-1-naphthol 

Relevant academic research and scientific papers

Nickel Carbodicarbene Catalyzes Kumada Cross-Coupling of Aryl Ethers with Grignard Reagents through C–O Bond Activation

The development of a cross-coupling reaction protocol between aryl ethers and Grignard reagents catalyzed by carbodicarbene (CDC) nickel complexes to afford biaryl compounds through C–O cleavage is reported. Aromatic substrates featuring a broad range of electron neutral, donating, or withdrawing groups are introduced at the desired position. The method has proven effective over a wide range of naphthyl methyl ethers, anisoles, and Grignard reagents. The robustness of the protocol is validated by performing multiple cleavage reactions, gram scale synthesis, and arylation of a dimethoxy esterdiol derivative.

Revisitation of Organoaluminum Reagents Affords a Versatile Protocol for C-X (X = N, O, F) Bond-Cleavage Cross-Coupling: A Systematic Study

A revisit of organoaluminum reagents for cross-coupling reactions has opened up several types of C-C bond formation protocols through cleavage of phenolic/alcoholic C-O and C-F and ammonium C-N bonds. Catalyzed by the commercially available NiCl2(PCy3)2 catalyst, these reactions proceed smoothly with a wide range of substrates and broad functional group compatibility, providing a versatile methodology for organoaluminum-mediated cross-coupling processes.

Excited state intramolecular proton transfer (ESIPT) from phenol to carbon in selected phenylnaphthols and naphthylphenols

ESIPT and solvent-assisted ESPT in isomeric phenyl naphthols and naphthyl phenols 5-8 were investigated by preparative photolyses in CH 3CN-D2O, fluorescence spectroscopy, LFP, and ab initio calculations. ESIPT takes place only in 5 (D-exchange Φ = 0.3), whereas 6-8 undergo solvent-assisted PT with much lower efficiencies. The efficiency of the ESIPT and solvent-assisted PT is mainly determined by different populations of the reactive conformers in the ground state and the NEER principle. The D-exchange experiments and calculations using RI-CC2/cc-pVDZ show that 5 in S1 deactivates by direct ESIPT from the OH to the naphthalene position 1 through a conical intersection with S0, delivering QM 14 that was detected by LFP (τ = 26 ± 3 ns). ESIPT to position 3 in 5 is possible but it proceeds from a less-populated conformer and involves an energy barrier on S1. In solvent-assisted PT to naphthalene position 4 in 5, zwitterion 17 is formed, which cyclizes to stable naphthofuran photoproducts 9-12. The regiochemistry of the deuteration in solvent-assisted PT was correlated with the NBO charges of the corresponding phenolates/naphtholates 5--8-. Combined experimental and theoretical data indicate that solvent-assisted PT takes place via a sequential mechanism involving first deprotonation of the phenol/naphthol, followed by the protonation by H 2O in the S1 state of phenolate/naphtholate. The site of protonation by H2O is mostly at the naphthalene α-position.

An efficient suzuki-miyaura coupling of aryl sulfamates and boronic acids catalyzed by NiCl2(dppp)

The Suzuki-Miyaura cross-coupling of aryl sulfamates and boronic acids was investigated by using [1,3-bis(diphenylphosphanyl)propane]nickel(II) chloride {NiCl2(dppp)} as the catalyst. The results showed that NiCl 2(dppp) is a highly active and general catalyst that allows effective Suzuki-Miyaura cross-coupling of aryl sulfamates with a slight excess amount of the boronic acid (1.2 equiv.) in the presence of a low catalyst loading (generally 1.0-1.5 mol-%). The method also displays broad generality not only to various aryl sulfamates, but also to an array of boronic acids. Furthermore, various functional groups are tolerated. These apparent advantages make NiCl2(dppp) a practical and reliable catalyst system for the Suzuki-Miyaura coupling of aryl sulfamates.

ORGANOMETALLIC COMPLEX FOR ORGANIC LIGHT-EMITTING LAYER AND ORGANIC LIGHT-EMITTING DIODE USING THE SAME

An organometallic complex represented by Formula 1 is provided. An organic light-emitting diode using the organometallic complex exhibits improved current and power efficiency and long lifetime.

Stabilization of excited state using through-space interaction between independent π-systems mediated by a peri-substituted hydroxy group in 1-arylnaphthalenes: Unexpected blue emission of 1,3,5-tris(peri-hydroxynaphthyl) benzene

The control of photoluminescence wavelength is important for the design of emitting materials, and compounds bearing arylaryl bonds are considered to be useful candidates for the synthesis of these materials. However, the biaryl system lacks an efficient

CROSS-COUPLING OF PHENOLIC DERIVATIVES

Embodiments of the invention provide methods and materials for chemical cross-coupling reactions that utilize unconventional phenol derivatives as cross-coupling partners. Embodiments of the invention can be used to synthesize a variety of useful organic compounds, for example the anti-inflammatory drug flurbiprofen.

Suzuki-Miyaura cross-coupling of aryl carbamates and sulfamates: Experimental and computational studies

The first Suzuki-Miyaura cross-coupling reactions of the synthetically versatile aryl O-carbamate and O-sulfamate groups are described. The transformations utilize the inexpensive, bench-stable catalyst NiCl 2(PCy3)2 to furnish biaryls in good to excellent yields. A broad scope for this methodology has been demonstrated. Substrates with electron-donating and electron-withdrawing groups are tolerated, in addition to those that possess ortho substituents. Furthermore, heteroaryl substrates may be employed as coupling partners. A computational study providing the full catalytic cycles for these cross-coupling reactions is described. The oxidative addition with carbamates or sulfamates occurs via a five-centered transition state, resulting in the exclusive cleavage of the aryl C-O bond. Water is found to stabilize the Ni-carbamate catalyst resting state, which thus provides rationalization of the relative decreased rate of coupling of carbamates. Several synthetic applications are presented to showcase the utility of the methodology in the synthesis of polysubstituted aromatic compounds of natural product and bioactive molecule interest.

A highly para-selective copper(II)-catalyzed direct arylation of aniline and phenol derivatives

In short order: A copper-catalyzed Friedel-Crafts-type strategy has been developed for the title reaction. An iterative C-H arylation strategy has also been demonstrated for the functionalization of anilines by sequentially delivering different aromatic groups to the para, ortho, and meta positions (see scheme, Bn=benzyl, Piv=pivaloyl).

Suzuki-Miyaura coupling of aryl carbamates, carbonates, and sulfamates

(Chemical Equation Presented) The first Suzuki-Miyaura cross-couplings of carbamates, carbonates, and sulfamates is described. The method provides a powerful means of using simple derivatives of phenol as precursors to polysubstituted aromatic compounds, as exemplified by a concise synthesis of the anti-inflammatory drug flurbiprofen.