7497-60-1Relevant articles and documents
Dirhodium-Catalyzed Enantioselective B?H Bond Insertion of gem-Diaryl Carbenes: Efficient Access to gem-Diarylmethine Boranes
Huang, Ming-Yao,Li, Xiao-Yu,Su, Yu-Xuan,Yang, Liang-Liang,Zhao, Yu-Tao,Zhu, Shou-Fei
, p. 24214 - 24219 (2021/10/07)
The scarcity of reliable methods for synthesizing chiral gem-diarylmethine borons limits their applications. Herein, we report a method for highly enantioselective dirhodium-catalyzed B?H bond insertion reactions with diaryl diazomethanes as carbene precursors. These reactions afforded chiral gem-diarylmethine borane compounds in high yield (up to 99 % yield), high activity (turnover numbers up to 14 300), high enantioselectivity (up to 99 % ee) and showed unprecedented broad functional group tolerance. The borane compounds synthesized by this method could be efficiently transformed into diaryl methanol, diaryl methyl amine, and triaryl methane derivatives with good stereospecificity. Mechanistic studies suggested that the borane adduct coordinated to the rhodium catalyst and thus interfered with decomposition of the diazomethane, and that insertion of a rhodium carbene (generated from the diaryl diazomethane) into the B?H bond was most likely the rate-determining step.
Recyclable polyetheretherketone fiber-supported N-heterocyclic carbene catalysts for nucleophilic acylation of fluorobenzenes
Shi, Xian-Lei,Sun, Benyu,Hu, Qianqian,Liu, Kun,Li, Pengyu,Wang, Juanjuan
supporting information, p. 11390 - 11393 (2020/10/12)
We report for the first time a novel support of polyetheretherketone fiber for the synthesis of recyclable N-heterocyclic carbene (NHC) catalysts. The fiber catalysts were verified in nucleophilic acylation of fluorobenzenes with superior catalytic activities, and successfully recycled by a tiny pair of tweezers over 21 cycles with minimal loss of performance.
α-Chlorobenzylation of Nitroarenes via Vicarious Nucleophilic Substitution with Benzylidene Dichloride: Umpolung of the Friedel-Crafts Reaction
Brze?kiewicz, Jakub,Loska, Rafa?,Makosza, Mieczys?aw
, p. 8499 - 8508 (2018/06/25)
Readily available α,α-dichlorotoluenes enter a vicarious nucleophilic substitution (VNS) reaction with electron-deficient arenes to give α-chlorobenzylated nitrobenzenes, as well as six- and five-membered heterocycles. Oxidation of the initially formed α-chlorobenzylic carbanions instead of protonation results in formation of diaryl ketones, providing a means for overall nucleophilic C-H benzoylation of electron-deficient aromatic rings. Alternatively, benzoylated nitroarenes can be obtained via the reaction of isolated α-chlorodiarylmethanes with sodium azide.