671-14-7Relevant academic research and scientific papers
Photoredox-Catalyzed Synthesis of α-Amino Acid Amides by Imine Carbamoylation
Cardinale, Luana,Schmotz, Mattis-Ole W. S.,Konev, Mikhail O.,Jacobi von Wangelin, Axel
supporting information, p. 506 - 510 (2022/01/20)
An operationally simple protocol for the photocatalytic carbamoylation of imines is reported. Easily available, bench-stable 4-amido Hantzsch ester derivatives serve as precursors to carbamoyl radicals that undergo rapid addition to N-aryl imines. The reaction proceeds under blue light irradiation in the presence of the photocatalyst 3DPAFIPN and Br?nsted/Lewis acid additives. Mechanistic studies indicated a photoredox mechanism that involves carbamoyl radicals.
Synthesis and application of axially chiral biscarbolines with functional N-O and sulfone for 1,2-transfer hydrogenations of ketimines
Xing, Yongfei,Wu, Shijie,Dong, Mengxian,Wang, Jie,Liu, Li,Zhu, Huajie
supporting information, (2019/08/08)
A series of axially chiral biscarboline-based sulfones were synthesized from L-tryptophane and applied for enantioselective 1,2-transfer hydrogenations of ketimines using trichlorosilane. The catalyst 4e, which had a tertiary butyl group, exhibited a good conversion and high enantioselectivities up to 96%ee in the series of reactions.
Mono- and diylide-substituted phosphines (YPhos): Impact of the ligand properties on the catalytic activity in gold(i)-catalysed hydroaminations
Schwarz, Christopher,Handelmann, Jens,Baier, Daniel M.,Ouissa, Alina,Gessner, Viktoria H.
, p. 6808 - 6815 (2019/12/03)
Understanding the impact of ligand properties on their performance in catalysis is seminal for future ligand design and catalyst improvement. In this work, the influence of the steric and electronic properties on the efficiency of a series of mono- and di
An efficient proline-based homogeneous organocatalyst with recyclability
Li, Qiang,Li, Yuan,Wang, Jingdong,Lin, Yingjie,Wei, Zhonglin,Duan, Haifeng,Yang, Qingbiao,Bai, Fuquan,Li, Yaoxian
supporting information, p. 827 - 831 (2018/02/03)
In this work, a homogeneous organocatalyst was developed for the asymmetric reduction of imines. This catalyst could be separated by cyclodextrin-modified Fe3O4@SiO2 magnetic nanoparticles and then released back into a fre
Thiolate-Protected Au 25 (SC 2 H 4 Ph) 18 Nanoclusters as a Catalyst for Intermolecular Hydroamination of Terminal Alkynes
Nagata, Tatsuki,Adachi, Yurina,Obora, Yasushi
, p. 2655 - 2659 (2018/12/14)
Au 25 (SC 2 H 4 Ph) 18 nanoclusters have high catalytic activity for hydroamination of terminal alkynes. This reaction proceeds under O 2 or air. The presence of molecular oxygen has a profound effect
Neutral and cationic cyclic (alkyl)(amino)carbene mercury [cAAC-Hg(ii)] complexes: Scope of hydroamination of alkynes with organomercury compounds
Bawari, Deependra,Goswami, Bhupendra,Sabari,Thakur, Sandeep Kumar,Varun Tej,Roy Choudhury, Angshuman,Singh, Sanjay
supporting information, p. 6274 - 6278 (2018/05/23)
This study demonstrates the first synthesis of cyclic (alkyl)(amino)carbene (cAAC) adducts of Hg(ii), [cAACMe·HgBr(μ-Br)]2 (1a) and [cAACcy·HgBr(μ-Br)]2 (1b). Adduct 1b catalyzes intermolecular hydroamination of
Ylide-Functionalized Phosphines: Strong Donor Ligands for Homogeneous Catalysis
Scherpf, Thorsten,Schwarz, Christopher,Scharf, Lennart T.,Zur, Jana-Alina,Helbig, Andreas,Gessner, Viktoria H.
supporting information, p. 12859 - 12864 (2018/09/25)
Phosphines are important ligands in homogenous catalysis and have been crucial for many advances, such as in cross-coupling, hydrofunctionalization, or hydrogenation reactions. Herein we report the synthesis and application of a novel class of phosphines bearing ylide substituents. These phosphines are easily accessible via different synthetic routes from commercially available starting materials. Owing to the extra donation from the ylide group to the phosphorus center the ligands are unusually electron-rich and can thus function as strong electron donors. The donor capacity surpasses that of commonly used phosphines and carbenes and can easily be tuned by changing the substitution pattern at the ylidic carbon atom. The huge potential of ylide-functionalized phosphines in catalysis is demonstrated by their use in gold catalysis. Excellent performance at low catalyst loadings under mild reaction conditions is thus seen in different types of transformations.
“Half-sandwich” Schiff-base Ir(III) complexes as anticancer agents
Mou, Ze-dong,Deng, Ning,Zhang, Feng,Zhang, Jiaying,Cen, Juan,Zhang, Xia
, p. 72 - 82 (2017/06/27)
A series of “half-sandwich” Schiff-base Ir(III) complexes were synthesized and investigated for their in vitro activities against the leukemia K562 cell line. These compounds demonstrated antiproliferative activities against K562 cells with IC50 values of 0.26–4.77 μM. In particular, compound 10c showed cytotoxicity against five cancer cell lines/sublines and stronger activities than cisplatin in K562, K562/A02, MCF-7, MCF-7/ADM, and A549 cells. Mechanism studies illustrated that compound 10c increased the level of reactive oxygen species and induced apoptosis of K562 cells. This compound effectively decreased the mitochondrial membrane potential and the protein level of Bcl-2. It also increased the protein levels of Bax, caspase-3, and caspase-9, and led to release of cytochrome c in K562 cells, indicating that the apoptosis induced by compound 10c was mediated by the intrinsic mitochondria apoptosis pathway.
From Ketones, Amines, and Carbon Monoxide to 4-Quinolones: Palladium-Catalyzed Oxidative Carbonylation
Wu, Jiwei,Zhou, Yuchen,Wu, Ting,Zhou, Yi,Chiang, Chien-Wei,Lei, Aiwen
supporting information, p. 6432 - 6435 (2017/12/08)
A novel method of palladium-catalyzed oxidative carbonylation of ketones, amines, and carbon monoxide for the synthesis of 4-quinolones has been developed. This protocol provides a straightforward route to construct useful 4-quinolone derivatives from ine
Palladium-catalyzed aerobic oxidative hydroamination of vinylarenes using anilines: A wacker-type amination pathway
Song, Eunsun,Kim, Hun Young,Oh, Kyungsoo
supporting information, p. 5264 - 5267 (2017/11/06)
A palladium-catalyzed intermolecular hydroamination of vinylarene derivatives using anilines has been developed for the first time under aerobic conditions, where the regioselective formation of N-arylketimines is accomplished. The current aerobic oxidative hydroamination pathway of anilines is distinct from that of palladiumcatalyzed hydroamination reactions that proceed to give sec-arylethylamine and arylethylamine derivatives, identifying a longstanding missing reaction pathway, Wacker-type amination, to N-arylketimines using anilines. The ready availability of both starting materials, vinylarenes and anilines, offers an attractive and facile synthetic route to N-arylketimines in good to excellent yields.
