101104-31-8Relevant articles and documents
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Pratt,Botimer
, p. 5248 (1957)
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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
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
