1674-30-2Relevant articles and documents
In Situ Formation and Reactions of Chloromethyl-lithium under Sonochemical Conditions
Einhorn, Cathy,Allavena, Corinne,Luche, Jean-Louis
, p. 333 - 334 (1988)
Under sonication, bromochloromethane, a carbonyl compound, and lithium in tetrahydrofuran yield the corresponding α-chlorohydrin, which can cyclise to the epoxide, in excellent yields.
Dihydroxylation of styrene by sodium chlorite with scandium triflate
Ohkubo, Kei,Hirose, Kensaku,Shibata, Takekatsu,Takamori, Kiyoto,Fukuzumi, Shunichi
, (2017)
Dihydroxylation of styrene by chlorite (ClO2 ?) with scandium triflate [Sc(OTf)3] occurs efficiently to produce 1-phenylethane-1,2-diol under the ambient conditions. Scandium triflate acting as a strong Lewis acid is found to accelerate the disproportionation of ClO2 ? to produce ClO? and ClO3 ?. A scandium-chlorine dioxide complex (Sc3+ClO2 ?) is generated by the reaction of ClO? with ClO2 ? in the presence of Sc3 +. The binding of Sc3 + to ClO2 ? was detected by the electron paramagnetic resonance measurements, enhancing the reactivity and selectivity of styrene hydroxylation.
A phosphonium ylide as a visible light organophotoredox catalyst
Toda, Yasunori,Tanaka, Katsumi,Matsuda, Riki,Sakamoto, Tomoyuki,Katsumi, Shiho,Shimizu, Masahiro,Ito, Fuyuki,Suga, Hiroyuki
supporting information, p. 3591 - 3594 (2021/04/14)
A phosphonium ylide-based visible light organophotoredox catalyst has been designed and successfully applied to halohydrin synthesis using trichloroacetonitrile and epoxides. An oxidative quenching cycle by the ylide catalyst was established, which was confirmed by experimental mechanistic studies.
Chiral aminoalcohols and squaric acid amides as ligands for asymmetric borane reduction of ketones: Insight to in situ formed catalytic system by DOSY and multinuclear NMR experiments
Dobrikov, Georgi M.,Nikolova, Yana,Petkova, Zhanina,Shestakova, Pavletta
supporting information, (2021/11/27)
A series of squaric acid amides (synthesized in 66–99% isolated yields) and a set of chiral aminoalcohols were comparatively studied as ligands in a model reaction of reduction of α-chloroacetophenone with BH3?SMe2. In all cases, the aminoalcohols demonstrated better efficiency (up to 94% ee), while only poor asymmetric induction was achieved with the corresponding squaramides. A mechanistic insight on the in situ formation and stability at room temperature of intermediates generated from ligands and borane as possible precursors of the oxazaborolidine-based catalytic system has been obtained by1H DOSY and multinuclear 1D and 2D (1H,10/11B,13C,15N) NMR spectroscopy of equimolar mixtures of borane and selected ligands. These results contribute to better understanding the complexity of the processes occurring in the reaction mixture prior to the possible oxazaborolidine formation, which play a crucial role on the degree of enantioselectivity achieved in the borane reduction of α-chloroacetophenone.
Organomagnesium Based Flash Chemistry: Continuous Flow Generation and Utilization of Halomethylmagnesium Intermediates
Von Keutz, Timo,Cantillo, David,Kappe, C. Oliver
supporting information, p. 7537 - 7541 (2020/10/12)
The generation of highly unstable chloromethylmagnesium chloride in a continuous flow reactor and its reaction with aldehydes and ketones is reported. With this strategy, chlorohydrins and epoxides were synthesized within a total residence time of only 2.6 s. The outcome of the reaction can be tuned by simply using either a basic or an acidic quench. Very good to excellent isolated yields, up to 97%, have been obtained for most cases (30 examples).
