66464-22-0Relevant academic research and scientific papers
Lateral lithiation in deep eutectic solvents: regioselective functionalization of substituted toluene derivatives
Arnodo, Davide,Blangetti, Marco,Ghinato, Simone,Nejrotti, Stefano,Prandi, Cristina
supporting information, p. 2391 - 2394 (2020/03/06)
The heteroatom-directed lateral lithiation of functionalized toluenes in a choline chloride-based eutectic mixture is reported. The metalations proceed within ultrafast reaction times, with a broad substrate and electrophile scope. The directing groups pr
Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter
Chen, Xiao,Li, Jiao-Jie,Hao, Xue-Shi,Goodhue, Charles E.,Yu, Jin-Quan
, p. 78 - 79 (2007/10/03)
The combination of directed C-H activation, batch-wise addition of tetraalkyltin reagents, and rate enhancement by benzoquinone and microwave irradiation provides a promising strategy for the direct coupling of C-H bonds with organometallic reagents. A variety of tetraalkyltins were coupled to C-H bonds to give the alkylated products in good yields by using 5 mol % Pd(OAc)2 as the catalyst. Benzoquinone was shown to be essential for the C-H activation when substrates containing non-π-conjugated chelating groups are used. Monitoring the formation and reductive elimination of the Pd(Ar)(Me)L2 complex also revealed that benzoquinone promotes the reductive elimination step. Microwave irradiation enhances the reaction rate drastically. The versatility of this protocol was demonstrated by using substrates containing either oxazoline or pyridine as directing groups. Copyright
Optional ortho and lateral lithiations of 4,4-dimethyl-2-(o-tolyl)oxazolines
Tahara, Naruki,Fukuda, Tsutomu,Iwao, Masatomo
, p. 9069 - 9072 (2007/10/03)
4,4-Dimethyl-2-(o-tolyl)oxazolines 1 undergo normal lateral lithiation at the benzylic position by treatment with sec-BuLi in diethyl ether at -78°C. In contrast, metalation of 1 with sec-BuLi/TMEDA in diethyl ether at the same temperature leads to ortho-
The Reactions of Carbene Intermediates from the Reaction of Trialkyl Phosphites with Dialkyl Benzoylphosphonates: Intramolecular Cyclisations of 2-Substituted Dialkyl Benzoylphosphonates
Griffiths, D. Vaughan,Griffiths, Penelope A.,Karim, Khalku,Whitehead, Belinda J.
, p. 901 - 925 (2007/10/03)
The reaction of dialkyl aroylphosphonates 1 with trialkyl phosphites leads to the formation of carbene intermediates 3 via the anionic intermediates 2.The carbene intermediates 3 (R = 2-Me, 2-Prn, 2-Bun, 2-MeS, 2-EtO and 2-EtS) have
