5580-44-9Relevant academic research and scientific papers
Fe-catalyzed Fukuyama-type indole synthesis triggered by hydrogen atom transfer
Huang, Hanmin,Yu, Min,Zhang, Tianze
, p. 10501 - 10505 (2021/08/20)
Fe, Co, and Mn hydride-initiated radical olefin additions have enjoyed great success in modern synthesis, yet the extension of other hydrogen radicalophiles instead of olefins remains largely elusive. Herein, we report an efficient Fe-catalyzed intramolec
Nickel-catalyzed C3-alkylation of indoles with alcohols: Via a borrowing hydrogen strategy
Hu, Miao,Jiang, Yong,Sun, Nan,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan,Jin, Liqun
, p. 10057 - 10062 (2021/06/15)
An efficient method for the Ni-catalyzed C3-alkylation of indoles using readily available alcohols as the alkylating reagents has been developed. The alkylation was addressed with an air and moisture-stable binuclear nickel complex ligated by tetrahydroquinolin-8-one as the effective pre-catalyst. The newly developed transformation could accommodate a broad substrate scope including primary/secondary benzylic and aliphatic alcohols and substituted indoles. Mechanistic studies suggested that the reaction proceeds through a borrowing hydrogen pathway.
Nickel-catalysed chemoselective C-3 alkylation of indoles with alcohols through a borrowing hydrogen method
Adhikari, Debashis,Bains, Amreen K.,Biswas, Ayanangshu
supporting information, p. 15442 - 15445 (2020/12/25)
An inexpensive, air-stable, isolable nickel catalyst is reported that can perform chemoselective C3-alkylation of indoles with a variety of alcohols following "borrowing hydrogen". A one-pot, cascade C3-alkylation starting from 2-aminophenyl ethyl alcohols, and thus obviating the need for pre-synthesized indoles, further adds to the broad scope of this method. The reaction is radical-mediated, and is significantly different from other examples, often dictated by metal-ligand bifunctionality. This journal is
Bifunctional Iron Complexes Catalyzed Alkylation of Indoles
Seck, Charlotte,Mbaye, Mbaye Diagne,Gaillard, Sylvain,Renaud, Jean-Luc
supporting information, p. 4640 - 4645 (2018/10/31)
Cyclopentadienone iron carbonyl complexes have been applied in alkylation of indoles with various benzylic alcohols, aliphatic alcohols (butanol, ethanol, methanol and 2-methylpentanol) via the hydrogen autotransfer strategy in mild reaction conditions. Experimental works highlight the role of the bifunctional iron complexes and the base. These iron complexes demonstrated a broad applicability in mild conditions and extended the scope of substrates in iron catalyzed C?C bond formation. (Figure presented.).
Environmentally friendly and regioselective C3-alkylation of indoles with alcohols through a hydrogen autotransfer strategy
Cano, Rafael,Yus, Miguel,Ramón, Diego J.
supporting information, p. 3394 - 3397 (2013/07/11)
The direct alkylation of indoles using KOH and alcohols, as initial source of the electrophile, under solvent-free conditions is a safe and environmentally benign strategy for selective modification of these structures at the C 3-position, without using hazardous and difficult to handle bromide or iodide derivatives or toxic and expensive transition metal catalysts. The protocol shows a broad scope, including halogenated indoles and secondary alcohols.
Transition-Metal-Catalyzed Regioselective Alkylation of Indoles with Alcohols
Putra, Anggi Eka,Takigawa, Kei,Tanaka, Hatsuki,Ito, Yoshihiko,Oe, Yohei,Ohta, Tetsuo
, p. 6344 - 6354 (2013/10/21)
The regioselective alkylation of indoles with alcohols as alkylating reagents was developed by using Pd/C or RuCl2(PPh3) 3/DPEphos {DPEphos = bis[(2-diphenylphosphanyl)phenyl] ether}as catalysts. The reaction of indole with benzyl alcohol in the presence of Pd/C and K2CO3 at 80 °C for 24 h without any solvent under in air yielded 90 % of 3-benzylindole. The corresponding 3-benzylindole was obtained in 99 % yield when the reaction was catalyzed by RuCl 2(PPh3)3/DPEphos in the presence of K 3PO4 at 165 °C for 24 h under argon. Several types of alcohols were treated with indoles under these conditions to give the corresponding 3-alkylated indoles in high yields (up to 99 %). This reaction may involve the catalyst-mediated transformation of alcohols to aldehydes, nucleophilic addition of indole to the resulting aldehydes accompanied by dehydration, and then hydrogenation. Copyright
Chemistry of indoles carrying basic functions. I. Transformation of hydroxyindolones into indoles
Moldvai, Istvan,Gacs-Baitz, Eszter,Szantay, Csaba
, p. 437 - 440 (2007/10/02)
3-Hydroxy-3--1H-indol-2-ones (1, 12) have been reduced with NaBH4/MeOH/t-BuOH.After acidic treatment, 2- and 3-substituted indoles (2, 11 and 13, 14, respectively) were obtained.The intermediates 3 and 4 of the rearrangenment were isolated and the effect of the pyridylmethyl groups on the rearrangenment has also been established.
BORONATION-THALLATION, A NEW APPROACH TO THE SYNTHESIS OF INDOLES HAVING ARYL AND/OR A HETEROARYL SUBSTITUENT AT THE 4-POSITION
Somei, Masanori,Amari, Hirokuni,Makita, Yoshihiko
, p. 3971 - 3973 (2007/10/02)
A new coupling reaction for unsymmetrical biaryls was developed and applied successfully to the syntheses of 4-arylindoles.Photoreaction of 4-halogenoidoles also proved to be a useful method for preparing 4-substituted indoles.An alternative method for sy
