35003-56-6Relevant articles and documents
Stable carbamate pathway towards organic-inorganic hybrid perovskites and aromatic imines
Hur, Nam Hwi,Kim, Sun Joo,Lee, Byeongno,Lee, Kyu Hyung,Lim, Byung Wook,Nam, Wonwoo,Park, Hee Sun,Park, Young Jun
, p. 38055 - 38062 (2020/11/02)
Methyl ammonium methyl carbamate (MAC), formulated as CH3NH3+CH3NHCO2-, was synthesized by reacting liquid methylamine with supercritical CO2, and its structure was refined by single-crystal X-ray diffraction. MAC is a white crystalline salt and is as reactive as methylamine, and is a very efficient alternative to toxic methylamine. We were able to produce hybrid perovskite MAPbI3 (MA = methyl ammonium) by grinding MAC with PbI2 and I2 at room temperature, followed by storing the mixed powder. Moreover, this one-pot method is easily scalable for the large-scale synthesis of MAPbI3 in a small vessel. We have also investigated the reactivity of MAC towards aromatic aldehydes in the absence of solvent. The solventless reactions afforded imines as exclusive products with over 97% yield, which show higher selectivity than the methylamine-based synthesis. Complete conversions were typically accomplished within 3 h at 25 °C. The results of this study emphasize the importance of solid carbamates such as MAC to develop an environmentally friendly process for the synthesis of various amine-based materials on the industrial scale.
Stereocomplementary Synthesis of cis- and trans-2-(p-Bromophenyl)-5-methylthiazolidin-4-ones: Useful Umpolung-type Suzuki–Miyaura Cross-coupling Partner and Donor
Sasaki, Ryosuke,Nakatsuji, Hidefumi,Tanabe, Yoo
, p. 1112 - 1118 (2018/03/21)
Novel cis- and trans-2-(p-bromophenyl)-5-methylthiazolidin-4-ones, S,N-containing heterocyclic compounds, were provided in a cis-stereocomplementary and trans-stereocomplementary synthetic manner. cis-Selective cyclo-condensation proceeded between 2-sulfanylpropanoic acid (thiolactic acid) and an imine derived from 4-bromobenzaldehyde and methylamine, whereas Ti(OiPr)4 and Ti(OiBu)4-promoted trans-selective cyclo-condensation proceeded between benzyl 2-sulfanylpropanoate and the imine. The obtained cis- and trans-2-(p-bromophenyl)-5-methylthiazolidin-4-ones were successfully converted to 2-(3-furyl)phenyl derivatives and bis(pinacolato)diborane derivatives utilizing Suzuki–Miyaura and Miyaura–Ishiyama cross-coupling reactions, respectively, in an umpolung manner.
Four-Electron Electrocyclic Ring-Opening/Intermolecular [4+2] Cycloadditions of α-Hydroxycyclobutenones: Stereoselective Synthesis of Multiple Substituted δ-Lactams
Song, Peidong,Li, Qing,Wang, Congcong,Wu, Wenfa,Mao, Xu,Wang, Jiajia,Hu, Xiangdong
supporting information, p. 1208 - 1212 (2016/04/26)
A four-electron electrocyclic ring-opening/intermolecular [4+2] cycloaddition of α-hydroxycyclobutenones is reported. The reaction represents the first example for the intermolecular cycloaddition of the extensively studied enol-ketene intermediate, and provides a new synthetic route to multiply substituted δ-lactams in high stereoselectivity.