1150589-22-2Relevant academic research and scientific papers
Mechanistic elucidation of intramolecular aminoalkene hydroamination catalyzed by a tethered bis(ureate) complex: Evidence for proton-assisted C-N bond formation at zirconium
Leitch, David C.,Platel, Rachel H.,Schafer, Laurel L.
, p. 15453 - 15463 (2011)
A broad mechanistic investigation regarding hydroamination reactions catalyzed by a tethered bis(ureate) zirconium species, [ureate(2-)]Zr(NMe 2)2(HNMe2), is described. The cyclization of both primary and secondary aminoal
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.
Intramolecular hydroamination reactions catalyzed by zirconium complexes bearing bridged bis(phenolato) ligands
Zhang, Yu,Sun, Qiu,Wang, Yaorong,Yuan, Dan,Yao, Yingming,Shen, Qi
, p. 10541 - 10548 (2016/02/09)
Zirconium complexes stabilized by piperazidine- and imidazolidine-bridged bis(phenolato) ligands have been synthesized and characterized. Their activities in catalyzing intramolecular hydroamination reactions have been tested and compared, which reveals the significant role that the ancillary ligands play in influencing catalytic activities. Cationic species derived from zirconium dibenzyl complexes showed good activities in catalyzing intramolecular hydroamination reactions of both primary and secondary amines, and afforded the respective N-heterocycles in 85% to 99% yields. Moreover, this catalytic system also catalyzed sequential cyclization of primary aminodienes, and generated bicyclic tertiary amines in 94-99% yields.
Intramolecular hydroamination of aminoalkenes catalyzed by a cationic zirconium complex
Wang, Xinke,Chen, Zhou,Sun, Xiu-Li,Tang, Yong,Xie, Zuowei
supporting information; experimental part, p. 4758 - 4761 (2011/10/30)
A new cationic [N-O-S]zirconium complex (cat.) was developed to be an excellent catalyst for the intramolecular hydroamination of aminoalkenes with a large substrate scope from terminal alkenes to internal alkenes, and primary amines to secondary amines. The catalyst system can also tolerate various functional groups and perform sequential hydroamination of primary aminodienes.
Cu(I)-catalyzed intramolecular hydroamination of unactivated alkenes bearing a primary or secondary amino group in alcoholic solvents
Ohmiya, Hirohisa,Moriya, Toshimitsu,Sawamura, Masaya
supporting information; experimental part, p. 2145 - 2147 (2009/09/25)
The Cu-Xantphos system [Cu(O-t-Bu)-Xantphos, 10-15 mol%] catalyzes the intramolecular hydroamination of unactivated terminal alkenes bearing an unprotected aminoalkyl substituent in alcoholic solvents, giving pyrrolidine and piperidine derivatives in exce
Broadening the scope of group 4 hydroamination catalysis using a tethered ureate ligand
Leitch, David C.,Payne, Philippa R.,Dunbar, Christine R.,Schafer, Laurel L.
supporting information; experimental part, p. 18246 - 18247 (2010/04/25)
(Chemical Equation Presented) A broadly applicable group-4-based precatalyst for the hydroamination of primary and secondary amines was developed. Screening experiments involving a series of amide and urea proligands led to the discovery of a tethered bis(ureate) zirconium complex with unprecedented reactivity in the intermolecular hydroamination of alkynes and the intramolecular hydroamination of alkenes. This catalyst system is effective with primary and secondary amines, 1,2-disubstituted alkenes, and heteroatom-containing functional groups, including ethers, silanes, amines, and heteroaromatics. The gem-disubstituent effect is not required for cyclization. The catalyst is generally regioselective for the anti-Markovnikov product of intermolecular alkyne hydroamination, and chemoselective for hydroamination over C-alkylation when forming 6- and 7-membered rings from aminoalkenes.
