758640-21-0Relevant academic research and scientific papers
Imine hydrogenation by alkylaluminum catalysts
Hatnean, Jillian A.,Thomson, Jordan W.,Chase, Preston A.,Stephan, Douglas W.
, p. 301 - 303 (2014)
Di-isobutylaluminum hydride and tri-iso-butylaluminum (DIBAL 1, TIBAL 2) are shown to be efficient hydrogenation catalysts for a variety of imines at 100 °C and 100 atm of H2, operating via a hydroalumination/ hydrogenolysis mechanism.
Iodine-Mediated One-Pot Synthesis of 2-(Piperazin-1-yl)pyrazine Derivatives from N -Alkyl Piperazines
Liu, Ruihuan,Wang, Yikun,Weng, Yanmei,Yao, Caiping,Zhang, Yan,Zhu, Gangzhi,He, Xiaoai,Xu, Kangping,Tan, Guishan
, p. 1083 - 1086 (2017)
An iodine-mediated one-pot reaction of N-alkyl piperazines is described for the first time. This transformation provides a straightforward and facile pathway to the synthesis of 2-(piperazin-1-yl)pyrazine derivatives with the corresponding N-alkyl piperazines as single material. Based on a series of control experiments, a plausible reaction mechanism has been proposed.
Bioinspired synthesis of well faceted CuI nanostructures and evaluation of their catalytic performance for coupling reactions
Gao, Shuyan,Li, Zhengdao,Jia, Xiaoxia,Jiang, Kai,Zeng, Haibo
, p. 1442 - 1447 (2010)
Well faceted CuI, truncated tetrahedral nanocrystals, were fabricated by an ascorbic acid-assisted green strategy at room temperature in a short period of time. A possible growth mechanism of such highly faceted nanostructures based on typical biomolecule-crystal interactions in aqueous solution is tentatively proposed. The large surface area and rich exposed active sites are expected to endow such truncated tetrahedral nanostructures with excellent performances in catalysis, as demonstrated here for the remarkable catalytic activity with respect to the coupling reaction between benzylamine and iodobenzene. This interesting result highlights the advantage of such a CuI nanostructure over the bulk counterpart, i.e. the high density of active sites and large specific surface area, which places a solid foundation for the feasible and promising application of such highly faceted nanomaterials in catalysis. It is the first report on the nanometre-sized faceted CuI acting as a catalyst for a coupling reaction and simultaneously a good example for the combination of green chemistry and functional materials.
Copper(i)-catalysed intramolecular hydroarylation-redox cross-dehydrogenative coupling ofN-propargylanilines with phosphites
Li, Guangzhe,Yu, Guo,Wang, Chengdong,Morita, Taiki,Zhang, Xuhai,Nakamura, Hiroyuki
, p. 113 - 116 (2021/12/29)
Intramolecular hydroarylation-redox cross-dehydrogenative coupling ofN-propargylanilines with phosphite diesters proceeded in the presence of Cu(i)-catalysts (20 mol%) to selectively give 2-phosphono-1,2,3,4-tetrahydroquinolines in good yields with 100% atomic utilization. P-H and two C-H bonds are activated at once and these hydrogen atoms are trapped by a propargylic triple bond in the molecule.
Platinum Assisted Tandem P–C Bond Cleavage and P–N Bond Formation in Amide Functionalized Bisphosphine o-Ph2PC6H4C(O)N(H)C6H4PPh2-o: Synthesis, Mechanistic, and Catalytic Studies
Kunchur, Harish S.,Balakrishna, Maravanji S.
supporting information, p. 857 - 868 (2022/01/19)
The reactions of amide functionalized bisphosphine o-Ph2PC6H4C(O)N(H)C6H4PPh2-o (1) with platinum salts are described. Treatment of 1 with [Pt(COD)Cl2] yielded a chelate complex, [PtCl2{o-Ph2PC6H4C(O)N(H)C6H4PPh2-o}κ2-P,P] (2), which on subsequent treatment with LiHMDS formed a novel 1,2-azaphospholene-phosphine complex [Pt(C6H5)Cl{o-C6H4{C(O)N(o-PPh2(C6H4))P(Ph)}}κ2-P,P] (3) involving a tandem P–C bond cleavage and P–N bond formation. The same complex 3 on passing dry HCl gas afforded the dichloro complex [PtCl2{o-C6H4{C(O)N(o-PPh2(C6H4))P(Ph)}}κ2-P,P] (5). Complex 2 upon refluxing in toluene or treatment of 1 with [Pt(COD)Cl2] in the presence of a base at room temperature resulted in the pincer complex [PtCl{o-Ph2PC6H4C(O)N(C6H4PPh2-o)}κ3-P,N,P] (4). Reaction of 1 with [Pt(COD)ClMe] at room temperature also afforded the pincer complex [PtMe{o-Ph2PC6H4C(O)N(C6H4PPh2-o)}κ3-P,N,P] (6). Mechanistic studies on 1,2-azaphospholene formation showed the reductive elimination of LiCl to form a phosphonium salt that readily adds one of the P–C bonds oxidatively to the in situ generated Pt0 species to form a chelate complex 3. The analogous palladium complex [PdCl2{o-C6H4{C(O)N(o-PPh2(C6H4))P(Ph)}}κ2-P,P] (7) showed excellent catalytic activity toward N-alkylation of amines with alcohols with a very low catalyst loading (0.05 mol %), and the methodology is very efficient toward the gram-scale synthesis of many N-alkylated amines.
Selective C-C bonds formation, N-alkylation and benzo[d]imidazoles synthesis by a recyclable zinc composite
Zhu, Guanxin,Duan, Zheng-Chao,Zhu, Haiyan,Ye, Dongdong,Wang, Dawei
supporting information, p. 266 - 270 (2021/08/06)
Earth abundant metals are much less expensive, promising, valuable metals and could be served as catalysts for the borrowing hydrogen reaction, dehydrogenation and heterocycles synthesis, instead of noble metals. The uniformly dispersed zinc composites were designed, synthesized and carefully characterized by means of XPS, EDS, TEM and XRD. The resulting zinc composite showed good catalytic activity for the N-alkylation of amines with amines, ketones with alcohols in water under base-free conditions, while unsaturated carbonyl compounds could also be synthesized by tuning the reaction conditions. Importantly, it was the first time to realize the synthesis of 2-aryl-1H-benzo[d]imidazole derivatives by using this zinc composite under green conditions. Meanwhile, this zinc catalyst could be easily recovered and reused for at least five times.
Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions
Fang, Jing,Li, Ting,Ma, Xiang,Sun, Jiuchang,Cai, Lei,Chen, Qi,Liao, Zhiwen,Meng, Lingkui,Zeng, Jing,Wan, Qian
supporting information, p. 288 - 292 (2021/07/25)
A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.
Porous polymeric ligand promoted copper-catalyzed C-N coupling of (hetero)aryl chlorides under visible-light irradiation
Wang, Erfei,Chen, Kaixuan,Chen, Yinan,Zhang, Jiawei,Lin, Xinrong,Chen, Mao
, p. 17 - 21 (2020/11/04)
A porous polymeric ligand (PPL) has been synthesized and complexed with copper to generate a heterogeneous catalyst (Cu@PPL) that has facilitated the efficient C-N coupling with various (hetero)aryl chlorides under mild conditions of visible-light irradiation at 80 °C (58 examples, up to 99% yields). This method could be applied to both aqueous ammonia and substituted amines, and is compatible to a variety of functional groups and heterocycles, as well as allows tandem C-N couplings with conjunctive dihalides. Furthermore, the heterogeneous characteristic of Cu@PPL has enabled a straightforward catalyst separation in multiple times of recycling with negligible catalytic efficiency loss by simple filtration, affording reaction mixtures containing less than 1 ppm of Cu residue. [Figure not available: see fulltext.]
Product selective reaction controlled by the combination of palladium nanoparticles, continuous microwave irradiation, and a co-existing solid; ligand-free Buchwald-Hartwig aminationvs.aryne amination
Akiyama, Toshiki,Arai, Masayoshi,Arisawa, Mitsuhiro,Haneoka, Hitoshi,Harada, Kazuo,Murai, Kenichi,Murakami, Yosuke,Ohki, Yuuta,Ohta, Ryousuke,Sako, Makoto,Sirimangkalakitti, Natchanun,Suzuki, Takeyuki,Takahashi, Naoyuki,Takehara, Tsunayoshi,Yamada, Makito
supporting information, p. 8131 - 8137 (2021/10/29)
We have developed a continuous microwave irradiation-assisted Buchwald-Hartwig amination using our original Pd nanoparticle catalyst with a copper plate as a co-existing metal solid. In this methodology, a microwave-controlled product selectivity was achieved between Buchwald-Hartwig amination and aryne amination performed under strongly basic conditions and at a high reaction temperature, because a polar chemical species such as Ar-Pd-halogen might be activated selectively by microwave radiation. Moreover, our catalyst could be used repeatedly over 10 times, and the amount of Pd leaching could be suppressed to a low level.
Chemoselective synthesis of imine and secondary amine from nitrobenzene and benzaldehyde by Ni3Sn2 alloy catalyst supported on TiO2
Yamanaka, Nobutaka,Hara, Takayoshi,Ichikuni, Nobuyuki,Shimazu, Shogo
, (2021/04/05)
Ni3Sn2/TiO2 alloy catalyst prepared by hydrothermal method was applied for the direct one-pot reductive imination of benzaldehyde with nitrobenzene in the presence of H2 gas as a reducing agent. A desired imine, benzylideneaniline, was produced in an excellent yield of 90% without the formation of any by-products. This is due to the chemoselective molecular recognition of Ni3Sn2 alloy nanoparticles supported on TiO2 for the nitro group over the carbonyl group. By prolonging the reaction time, the desired imine was converted into the corresponding secondary amine, N-phenylbenzylamine, with a remarkably high yield of 80% through the catalytic hydrogenation of the C[dbnd]N bond. Finally, we demonstrated that it was easy to reuse the catalyst up to five times.
