774-91-4Relevant articles and documents
Design, scope and mechanism of highly active and selective chiral NHC-iridium catalysts for the intramolecular hydroamination of a variety of unactivated aminoalkenes
Foster, Daven,Gao, Pengchao,Zhang, Ziyun,Sipos, Gellért,Sobolev, Alexandre N.,Nealon, Gareth,Falivene, Laura,Cavallo, Luigi,Dorta, Reto
, p. 3751 - 3767 (2021/03/26)
Chiral, cationic NHC-iridium complexes are introduced as catalysts for the intramolecular hydroamination reaction of unactivated aminoalkenes. The catalysts show high activity in the construction of a range of 5- and 6-membered N-heterocycles, which are accessed in excellent optical purity, with various functional groups being tolerated with this system. A major deactivation pathway is presented and eliminated by using alternative reaction conditions. A detailed experimental and computational study on the reaction mechanism is performed providing valuable insights into the mode of action of the catalytic system and pointing to future modifications to be made for this catalytic platform.
On the Superior Activity of In(I) versus In(III) Cations Toward ortho-C-Alkylation of Anilines and Intramolecular Hydroamination of Alkenes
Li, Zhilong,Yang, Shengwen,Thiery, Guillaume,Gandon, Vincent,Bour, Christophe
supporting information, p. 12947 - 12959 (2020/11/23)
An efficient ortho-C-alkylation of unprotected anilines with a variety of styrenes and alkenes using a univalent cationic indium(I) catalyst is reported. Mechanistic studies revealed that the reaction likely proceeds via a tandem hydroamination/Hofmann-Martius rearrangement. The high compatibility between the cationic indium(I) complex and primary anilines led us to develop an In(I)+-catalyzed hydroamination of alkenes using unprotected primary and secondary alkenylamines. Computations support the catalytic activity of naked In(I)+ ions, with an outer sphere mechanism for the C-N bond formation and a potentially inner sphere protodemetallation.
Reductive amination/cyclization of levulinic acid to pyrrolidones: Versus pyrrolidines by switching the catalyst from AlCl3 to RuCl3 under mild conditions
Liu, Zhimin,Wu, Cailing,Luo, Xiaoying,Zhang, Hongye,Liu, Xinwei,Ji, Guipeng,Liu, Zhenghui
supporting information, p. 3525 - 3529 (2017/08/15)
Herein the reductive amination/cyclization of levulinic acid using phenylsilane was presented to selectively produce pyrrolidones versus pyrrolidines under mild conditions by switching the catalyst from AlCl3 to RuCl3. Using AlCl3 as the catalyst, pyrrolidones were solely obtained at room temperature, while RuCl3 as the catalyst selectively afforded pyrrolidines in high yields at 45 °C.