42353-96-8Relevant articles and documents
The Hiyama Cross-Coupling Reaction at Parts Per Million Levels of Pd: In Situ Formation of Highly Active Spirosilicates in Glycol Solvents
Ichii, Shun,Hamasaka, Go,Uozumi, Yasuhiro
supporting information, p. 3850 - 3854 (2019/11/11)
A palladium NNC-pincer complex at a 5 mol ppm loading efficiently catalyzed the Hiyama coupling reaction of aryl bromides with aryl(trialkoxy)silanes in propylene glycol to give the corresponding biaryls in excellent yields. This method was applied to the syntheses of adapalene and a biaryl-type liquid-crystalline compound, as well as to the derivatization of dextromethorphan and norfloxacin. ESI-MS and NMR analyses of the reaction mixture suggested the formation of pentacoordinate spirosilicate intermediates in situ. Preliminary theoretical studies revealed that the glycol-derived silicate intermediates formed in situ are quite reactive silicon reagents in the transmetalation step.
Cobalt-catalyzed annulation of aryl iodides with alkynes
Komeyama, Kimihiro,Kashihara, Tetsuya,Takaki, Ken
, p. 5659 - 5662 (2013/09/24)
A cobalt-catalyzed approach for the concise synthesis of naphthalenes by the annulation of aryl iodides with alkynes is disclosed. In the reaction, manganese reductant and MeCN solvent are necessary to proceed efficiently, which tolerates various functional groups, for example, boronate ester. Mechanistic investigation indicates that the transformation employs electrophilic aromatic substitution (SEAr) in the aromatic C-H bond replacement step.
Alkynes as activators in the nickel-catalysed addition of organoboronates to aldehydes
Takahashi, Go,Shirakawa, Eiji,Tsuchimoto, Teruhisa,Kawakami, Yusuke
, p. 1459 - 1461 (2007/10/03)
Alkynes act not as substrates but as co-catalysts in the presence of a nickel catalyst, an organoboronate and an aldehyde to promote the addition reaction between the substrates in combination with H2O. The Royal Society of Chemistry 2005.