78388-91-7Relevant academic research and scientific papers
PdX2/CuX2-catalyzed annulation of 2-ethynylbenzeneamines: Selective synthesis of 2-substituted 3-halo-1H-indoles
Tang, Shi,Xie, Ye-Xiang,Li, Jin-Heng,Wang, Nai-Xing
, p. 1841 - 1847 (2007)
A novel and effective protocol for the synthesis of 2-substituted 3-halo-1H-indoles by PdX2/CuX2-catalyzed annulations of 2-ethynylbenzeneamines has been developed. In the presence of PdX2 and CuX2, the annulati
Monohydride-Dichloro Rhodium(III) Complexes with Chiral Diphosphine Ligands as Catalysts for Asymmetric Hydrogenation of Olefinic Substrates
Higashida, Kosuke,Brüning, Fabian,Tsujimoto, Nagataka,Higashihara, Kenya,Nagae, Haruki,Togni, Antonio,Mashima, Kazushi
, p. 8749 - 8759 (2020/07/04)
We report full details of the synthesis and characterization of monohydride-dichloro rhodium(III) complexes bearing chiral diphosphine ligands, such as (S)-BINAP, (S)-DM-SEGPHOS, and (S)-DTBM-SEGPHOS, producing cationic triply chloride bridged dinuclear rhodium(III) complexes (1 a: (S)-BINAP; 1 b: (S)-DM-SEGPHOS) and a neutral mononuclear monohydride-dichloro rhodium(III) complex (1 c: (S)-DTBM-SEGPHOS) in high yield and high purity. Their solid state structure and solution behavior were determined by crystallographic studies as well as full spectral data, including DOSY NMR spectroscopy. Among these three complexes, 1 c has a rigid pocket surrounded by two chloride atoms bound to the rhodium atom together with one tBu group of (S)-DTBM-SEGPHOS for fitting to simple olefins without any coordinating functional groups. Complex 1 c exhibited superior catalytic activity and enantioselectivity for asymmetric hydrogenation of exo-olefins and olefinic substrates. The catalytic activity of 1 c was compared with that of well-demonstrated dihydride species derived in situ from rhodium(I) precursors such as [Rh(cod)Cl]2 and [Rh(cod)2]+[BF4]? upon mixing with (S)-DTBM-SEGPHOS under dihydrogen.
Rhodium(III)-catalyzed intermolecular cyclization of anilines with sulfoxonium ylides toward indoles
Shen, Zhihao,Pi, Chao,Cui, Xiuling,Wu, Yangjie
supporting information, p. 1374 - 1378 (2019/02/28)
Rhodium(III)-catalyzed synthesis of indole derivatives has been realized via cascade reaction of C–H alkylation/nucleophilic cyclization starting from readily available N-phenylpyridin-2-amines and sulfoxonium ylides. Notably, this transformation could smoothly proceed with high yields, good regioselectivity, and feature broad group tolerance and under redox-neutral condition to avoid external oxidant. The titled products are potentially important building blocks in the organic synthesis through various chemical transformations.
PtCl4-catalyzed cyclization of N-acetyl-2-alkynylanilines: A mild and efficient synthesis of N-acetyl-2-substituted indoles
Chaisan, Nattawadee,Kaewsri, Wilailak,Thongsornkleeb, Charnsak,Tummatorn, Jumreang,Ruchirawat, Somsak
, p. 675 - 680 (2018/01/18)
An efficient synthesis of N-acetyl-2-substituted indole derivatives via direct intramolecular hydroamination of N-acetyl-2-alkynylaniline derivatives was developed. The reaction could be applied to a wide range of substrates employing only 1–2 mol% of PtCl4 as the catalyst to furnish the desired indole products in moderate to excellent yields. The current protocol is efficient, reliable and scalable, and could serve as an important tool for convenient and rapid access to this important class of N-heterocyclic skeleton from readily available substrates.
Mild and efficient synthesis of indoles and isoquinolones via a nickel-catalyzed Larock-type heteroannulation reaction
Weng, Wei-Zhi,Xie, Jian,Zhang, Bo
supporting information, p. 3983 - 3988 (2018/06/08)
A simple and efficient approach for the preparation of substituted indoles and isoquinolones via a nickel-catalyzed Larock-type heteroannulation reaction is reported. This transformation employed air-stable and inexpensive Ni(dppp)Cl2 as a precatalyst and Et3N as a mild base. Moreover, the reaction occurs efficiently under mild conditions, and a wide range of substituted indoles and isoquinolones bearing various functional groups are obtained in moderate to excellent yields.
Ruthenium-Catalyzed Cycloisomerization of 2-Alkynylanilides: Synthesis of 3-Substituted Indoles by 1,2-Carbon Migration
Watanabe, Takuma,Mutoh, Yuichiro,Saito, Shinichi
supporting information, p. 7749 - 7752 (2017/06/21)
We developed ruthenium-catalyzed cycloisomerization of alkynylanilides that gave 3-substituted indoles in high yields. The reaction proceeded via the disubstituted vinylidene ruthenium complex that was formed by the 1,2-carbon migration.
Synthesis of substituted benzofurans and indoles by Zn-catalyzed tandem Sonogashira-cyclization strategy
Thankachan, Amrutha P.,Sindhu, Kallikkakam S.,Ujwaldev, Sankuviruthiyil M.,Anilkumar, Gopinathan
supporting information, p. 536 - 540 (2017/01/16)
Transition metal catalyzed cross-coupling reactions are one of the predominant strategies for the construction of heterocyclic structures which possess wide applications in the synthesis of natural products, pharmaceuticals, polymers, etc. Due to the vast importance of substituted benzofurans and indoles, numerous synthetic methodologies have been introduced for their synthesis. Among these methods, transition metal catalyzed cyclization reactions possess a unique position. In this manuscript, we disclose the first and efficient zinc-catalyzed protocol for the cyclization reactions of alkynes with 2-iodophenol and 2-iodoaniline leading to benzofurans and indoles respectively via a tandem Sonogashira coupling-cyclization process. Among the different metal catalysts, zinc has enormous potential due to its great availability, non-toxicity, eco-friendly and inexpensive nature. Zn(II) with N,N′-dimethylethylenediamine represents a suitable and efficient catalytic system for the desired tandem CC coupling-cyclization reactions, and a broad spectrum of functional groups are tolerated during the catalysis. A variety of substituted benzofurans and indoles have been successfully prepared in moderate to good yields under this new protocol.
Intramolecular cooperative C-C bond cleavage reaction of 1,3-dicarbonyl compounds with 2-iodoanilines to give o-(N-Acylamino)aryl ketones and multisubstituted indoles
Xing, Qi,Lv, Hui,Xia, Chungu,Li, Fuwei
, p. 8591 - 8596 (2015/06/02)
A copper-catalyzed C-C bond cleavage reaction of 1,3-dicarbonyl compounds with 2-iodoanilines was developed. In this process, the ortho effect played an important role in the reactivity and a new reaction pathway that involved a (2-aminophenyl)-bis-(1,3-dicarbonyl) copper species was clearly observed by a time-course HRMS analysis of the reaction mixture. Unlike the previous reports, both the nucleophilic and electrophilic parts of the 1,3-dicarbonyl compound were coupled with 2-iodoaniline by C-C bond cleavage to form o-(N-acylamino)aryl ketones, which could be efficiently converted into multisubstituted indoles.
Silver(I)-mediated C-H amination of 2-alkenylanilines: Unique solvent-dependent migratory aptitude
Youn, So Won,Ko, Tae Yun,Jang, Min Jung,Jang, Su San
supporting information, p. 227 - 234 (2015/01/30)
A highly effective silver(I)-mediated C-H amination of 2-alkenylanilines has been developed to afford a diverse range of substituted indoles. High functional group tolerance, broad substrate scope, simple/fast/high-yielding reaction, and recovery/reuse of the inexpensive silver oxidant are noteworthy. Furthermore, an uncommon migratory process of β-monosubstituted 2-alkenylanilines with solvent-dependence was demonstrated.
Oxidative annulation of anilides with internal alkynes using an (Electron-Deficient η5-cyclopentadienyl)rhodium(III) catalyst under ambient conditions
Hoshino, Yuki,Shibata, Yu,Tanaka, Ken
, p. 1577 - 1585 (2014/06/09)
A dinuclear (electron-deficient η5-cyclopentadienyl) rhodium(III) complex was synthesized on a preparative scale via the rhodium-catalyzed cross [2+2+1] cyclotrimerization of silylacetylenes and two alkynyl esters, leading to substituted silylf
