33104-31-3

Upstream product

• 580-13-2 2-bromonaphthalene 
• 122439-11-6 tributyl(3-methoxyphenyl)stannane 
• 858364-74-6 N,N-diethyl naphthalen-2-yl O-sulfamate 
• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 91-20-3 naphthalene 
• 766-85-8 3-methoxy-1-iodobenzene 
• 613-46-7 2-naphthalenecarbonitrile 
• 1003858-50-1 2-(3-methoxyphenyl)-5, 5-dimethyl-1,3,2-dioxaborinane 
• 74525-40-9 potassium 3-methoxybenzoate 
• 7385-85-5 naphthalen-2-yl tosylate 
• 79421-99-1 tris(3-methoxyphenyl)-1,3,5,2,4,6-trioxatriborinane 
• 135-19-3 β-naphthol 
• 612-55-5 2-iodonaphthalene 
• 93-04-9 2-Methoxynaphthalene 

Downstream Products

• 33104-32-4 β-(3-hydroxyphenyl)naphthalene 
• 933066-91-2 5-naphthalen-2-yl-2,2-diphenyl-2H-chromene 
• 933066-99-0 7-naphthalen-2-yl-2,2-diphenyl-2H-chromene 

Relevant academic research and scientific papers

Stille couplings in supercritical CO2 catalyzed with perfluoro-tagged and un-tagged Pd complexes

Stille CC-couplings in supercritical CO2 (scCO2) were performed with perfluoro-tagged and un-tagged Pd complexes in high yields. With fluoro-tagged complexes yields were generally slightly higher. A recycling of the perfluoro-tagged catalyst was also achieved.

Arylketones as Aryl Donors in Palladium-Catalyzed Suzuki-Miyaura Couplings

Herein, we report the arylation, alkylation, and alkenylation of aryl ketones via a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. The use of the pyridine-oxazoline ligand is the key to the cleavage of the unstrained C-C bond. The late-stage arylation of aryl ketones derived from drugs and natural products demonstrated the synthetic utility of this protocol.

Palladium-catalyzed decarbonylative suzuki-miyaura coupling of amides to achieve biaryls via C-N bond cleavage

The palladium-catalyzed decarbonylative Suzuki-Miyaura coupling of amides via selective amide C-N bond cleavage was reported, which afforded mild access to substitute biaryl products in the presence of low catalyst loading with NaHCO3 as the base in good yields within 4 h (29 examples).

Nickel-Catalyzed Kumada Coupling of Boc-Activated Aromatic Amines via Nondirected Selective Aryl C-N Bond Cleavage

A nickel-catalyzed Kumada coupling of aniline derivatives was developed by selective cleavage of aryl C-N bonds under mild reaction conditions. Without preinstallation of an ortho directing group on anilines, the cross-coupling reactions of Boc-protected aromatic amines with aryl Grignard reagents afforded unsymmetric biaryls. Mechanistic studies by DFT calculations revealed that the nickel-mediated C-N bond cleavage is the rate-limiting step.

Chromium-Catalyzed Regioselective Kumada Arylative Cross-Coupling of C(aryl)-O Bonds with a Traceless Activation Strategy

We report here the chromium-catalyzed regioselective Kumada arylative cross-coupling of C(aryl)-O bonds at ambient temperature. By using a simple and low-cost chromium(II) chloride salt as a precatalyst, accompanied by a 2-pyridyl ligation, the catalytic cleavage and arylative coupling of C(aryl)-O bonds were achieved with a traceless activation strategy, overcoming the regioselectivity obstacle when several C-O bonds coexist in the Kumada coupling system.

Triarylphosphines as Aryl Donors for Pd(II)-Catalyzed Aromatic Coupling of Oxabenzonorbornadienes

A new approach was developed for Pd(II)-catalyzed aromatic coupling of oxabenzonorbornadienes with triarylphosphines as both ligands and aryl donors. Diverse functional groups including halo- (F-, Cl-, and Br-), CF3-, and furyl groups are well tolerated. For unsymmetrical triarylphosphines, the migration ability of aryls is consistent with the electronic property of substituents and maintains the order EDG-Ar > H-Ar > EWD-Ar (EDG means electron-donating group, EWG means electron-withdrawing group). A preliminary mechanistic study was also disclosed.

Improved procedure for single-electron-transfer-induced grignard cross-coupling reaction

Aryl Grignard reagents were found to undergo coupling with aryl or alkenyl bromides in the presence of LiCl in a mixed solvent consisting of toluene and THF (2/1). Previously employed removal of THF with evacuation from Grignard solutions is no longer needed to obtain biaryls and styrene derivatives.

Cross-coupling of aryl grignard reagents with aryl iodides and bromides through SRN1 pathway

Game, SET, and match: Aryl Grignard reagents undergo coupling with aryl halides when toluene is used as a solvent in combination with a small amount of tetrahydrofuran (see scheme). The reaction proceeds through an SRN1 mechanism, and does not require any transition metal catalysts.

Aryl ether as a Negishi coupling partner: An approach for constructing C-C bonds under mild conditions

An etheric Negishi coupling: The first cross-coupling reaction between aryl alkyl ethers and dianion-type zincate reagents to afford biaryl compounds through selective cleavage of the etheric C(sp2)-O bond was developed. Dianion-type zincates showed excellent reactivity toward the aromatic ethers under mild conditions, with good functional group compatibility (see scheme). Copyright

Mutual activation: Suzuki-Miyaura coupling through direct cleavage of the sp2 C-O bond of naphtholate

Working together: A new approach of mutual activation between naphtholates and aryl boronic acid derivatives by the formation of borates to facilitate the Suzuki-Miyaura coupling through direct cleavage of the sp2 C-O bond by nickel catalysis is described (see scheme; R′: annulated ring system). Various naphtholates and aryl boronic acid derivatives could be directly coupled in good yields. Copyright