3558-24-5Relevant articles and documents
Trans-Aminoboration across Internal Alkynes Catalyzed by B(C6F5)3 for the Synthesis of Borylated Indoles
Yuan, Kang,Wang, Suning
, p. 1462 - 1465 (2017)
We report here a facile B(C6F5)3 catalyzed trans-aminoboration of internal alkynes, furnishing 3-position borylated indoles at ambient temperature. This reaction proceeds with the breaking of a B-N bond and the formation of N-C and B-C bonds to produce indole and derivatives in one step. It works well for various boron reagents and alkynyl-anilines. The borylated indoles can be further derivatized to give column stable organoboron compounds that can be used for future functionalization.
A cyclization-rearrangement cascade for the synthesis of structurally complex chiral gold(I)-aminocarbene complexes
Kolundzic, Filip,Murali, Annamalai,Perez-Galan, Patricia,Bauer, Jonathan O.,Strohmann, Carsten,Kumar, Kamal,Waldmann, Herbert
, p. 8122 - 8126 (2014)
A facile synthesis of chiral cyclic alkyl aminocarbene-gold(I) complexes from gold-free 1,7-enyne substrates was developed. The novel cyclization-rearrangement reaction sequence is triggered by the addition of (Me2S)AuCl to different 1,7-enynes and leads to structurally unique carbene-gold(I) complexes in high yields. These novel complexes are catalytically active and inhibit the proliferation of different human cancer cell lines.
Structurally-defined direct C-magnesiation and C-zincation of N-heterocyclic aromatic compounds using alkali-metal-mediated metallation
Conway, Ben,Hevia, Eva,Kennedy, Alan R.,Mulvey, Robert E.
, p. 2864 - 2866 (2007)
Demonstrating direct synergic "low polarity metallation", 1-methylindole is C-magnesiated by (TMEDA)2·Na 2MgBu4 and C-zincated by (TMEDA)·Na( tBu)(TMP)Zn(tBu), and 1-methylpyrrole is C-zincated by the same reagent, with all three metal products successfully crystallographically characterised. The Royal Society of Chemistry.
Reaction of Phenacyltriphenylarsonium Bromides with N-Methylaniline and N,N-Dimethylaniline
Bansal, Raj Kumar,Bhagchandani, Gope
, p. 2423 - 2424 (1980)
Reaction of phenacyltriphenylarsonium bromide with N-methylaniline furnished 2-phenylindole predominantly together with 1-methyl-2-phenylindole.The corresponding reaction of the arsonium salt with N,N-dimethylaniline did not give any indole, instead a simple nucleophilic substituted product, α-4'-(dimethylamino)deoxybenzoin was obtained.But, the latter reaction on being carried out in presence of hydrobromic acid afforded 1-methyl-2-phenylindole by the demethylation of N,N-dimethylaniline.
PALLADIUM-PHOSPHINE COMPLEX CATALYZED CROSS-COUPLING REACTION OF 1-METHYL-2-PYRROLYL-MAGNESIUM BROMIDE AND -ZINC CHLORIDE WITH ORGANIC HALIDES
Minato, Akio,Tamao, Kohei,Hayashi, Tamio,Suzuki, Keizo,Kumuda, Makoto
, p. 5319 - 5322 (1981)
1-Methyl-2-pyrrolyl-magnesium bromide and -zinc chloride, which were prepared from 1-methyl-2-pyrrolyllithium with MgBr2 and ZnCl2 respectively, reacted with aryl- and heteroaromatic halides to give the corresponding 2-substituted pyrroles in good to excellent yields in the presence of palladium-phosphine complexes as catalysts.
Modular counter-Fischer?indole synthesis through radical-enolate coupling
Chung, Hyunho,Kim, Jeongyun,Gonzalez-Montiel, Gisela A.,Cheong, Paul Ha-Yeon,Lee, Hong Geun
supporting information, p. 1096 - 1102 (2021/01/26)
A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.
In Situ Preparation of Palladium Nanoparticles for C-2 Selective Arylation of Indoles in Agro-Waste Extract Based Mixed Solvents
Jin, Weiwei,Liu, Chenjiang,Liu, Tianxiang,Sun, Yajun,Wang, Bin,Wang, Rui,Xia, Yu,Zhang, Yonghong
supporting information, p. 2470 - 2473 (2021/06/25)
An efficient and practical method for the in situ generation of palladium nanoparticles was successfully established in a water extract of pomelo peel ash. The produced palladium nanoparticles were characterized by energy-dispersive X-ray spectroscopy elemental mapping, field emission scanning electron microscopy, high-resolution transmission electron microscope, X-ray powder diffraction, and showed high catalytic activity for selective C-2 arylation of indoles. A series of 2-arylindoles were smoothly installed in moderate to good yields through the direct palladium-catalyzed cross-coupling reactions of indoles and iodoarenes without external ligand, base, oxidant, and preinstallation directing group.
Tris-NHC-propagated self-supported polymer-based Pd catalysts for heterogeneous C-H functionalization
Choudhury, Joyanta,Dutta, Tapas Kumar,Mandal, Tanmoy,Mohanty, Sunit
supporting information, p. 10182 - 10185 (2021/10/12)
Three-dimensionally propagated imidazolium-containing mesoporous coordination polymer and organic polymer-based platforms were successfully exploited to develop single-site heterogenized Pd-NHC catalysts for oxidative arene/heteroarene C-H functionalization reactions. The catalysts were efficient in directed arene halogenation, and nondirected arene and heteroarene arylation reactions. High catalytic activity, excellent heterogeneity and recyclability were offered by these systems making them promising candidates in the area of heterogeneous C-H functionalization, where efficient catalysts are still scarce.
Regioselective Direct C2 Arylation of Indole, Benzothiophene and Benzofuran: Utilization of Reusable Pd NPs and NHC-Pd@MNPs Catalyst for C–H Activation Reaction
Hegde, Rajeev V.,Ong, Tiow-Gan,Ambre, Ram,Jadhav, Arvind H.,Patil, Siddappa A.,Dateer, Ramesh B.
, p. 1397 - 1405 (2020/10/02)
Abstract: A regioselective C2 arylation of indoles, benzothiophene and benzofuran without directing group has been accomplished using economically cheap Pd NPs and NHC-Pd@MNPs catalyst. The reusable catalyst is efficiently employed to access C2 arylated heterocycles in good to excellent yield. The reusability of the catalyst is studied up to five cycles and a gram-scale synthesis has been achieved. The reaction mechanism is well supported by control experiments and literature precedents. Grapic Abstract: [Figure not available: see fulltext.]
N-Hydroxyphthalimidyl diazoacetate (NHPI-DA): A modular methylene linchpin for the C-H alkylation of indoles
Chowdhury, Rajdip,Mendoza, Abraham
supporting information, p. 4532 - 4535 (2021/05/17)
Despite the extensive studies on the reactions between conventional diazocompounds and indoles, these are still limited by the independent synthesis of the carbene precursors, the specific catalysts, and the required multi-step manipulation of the products. In this work, we explore redox-Active carbenes in the expedited and divergent synthesis of functionalized indoles. NHPI-DA displays unusual efficiency and selectivity to yield insertion products that can be swiftly elaborated into boron and carbon substituents that are particularly problematic in carbene-mediated reactions.
