6908-75-4Relevant articles and documents
Insights into Rare-Earth Metal Complex-Mediated Hydroamination
Dong, Shuqi,Chen, Jinjin,Qiao, Kening,Fang, Jian,Yang, Yan,Maron, Laurent,Liu, Bo
, p. 3790 - 3800 (2021)
Since the precise understanding of the underlying mechanism is important for the rational design of catalysts, much attention has been paid for hydroamination reactions catalyzed by organolanthanides during the past three decades. Distinct mechanisms were
Two-Step Protocol for Iodotrimethylsilane-Mediated Deoxy-Functionalization of Alcohols
Chen, Yuming,He, Ru,Song, Hongjian,Yu, Guoqing,Li, Chenglin,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 1179 - 1183 (2021/02/01)
We have developed a two-step protocol for iodotrimethylsilane-mediated deoxy-functionalization of primary and secondary alcohols to afford products containing a C?N, C?S, or C?O bond. In the first step the alcohol undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non-acidic pre-nucleophiles can be used, and the reaction proceeds with retention of configuration. This operationally simple, highly efficient protocol can be used for some natural products and small-molecule drugs containing hydroxy-group.
Ambient Moisture Accelerates Hydroamination Reactions of Vinylarenes with Alkali-Metal Amides under Air
Bole, Leonie J.,Davin, Laia,García-álvarez, Joaquín,Hernán-Gómez, Alberto,Hevia, Eva,Kennedy, Alan,Mulks, Florian F.
supporting information, p. 19021 - 19026 (2020/09/01)
A straightforward alkali-metal-mediated hydroamination of styrenes using biorenewable 2-methyltetrahydrofuran as a solvent is reported. Refuting the conventional wisdom of the incompatibility of organolithium reagents with air and moisture, shown here is that the presence of moisture is key in favoring formation of the target phenethylamines over competing olefin polymerization products. The method is also compatible with sodium amides, with the latter showing excellent promise as highly efficient catalysts under inert atmosphere conditions.