- Nickel-catalyzed C3-alkylation of indoles with alcohols: Via a borrowing hydrogen strategy
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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.
- Hu, Miao,Jiang, Yong,Sun, Nan,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan,Jin, Liqun
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p. 10057 - 10062
(2021/06/15)
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- Nickel-catalysed chemoselective C-3 alkylation of indoles with alcohols through a borrowing hydrogen method
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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
- Adhikari, Debashis,Bains, Amreen K.,Biswas, Ayanangshu
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supporting information
p. 15442 - 15445
(2020/12/25)
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- General and selective C-3 alkylation of indoles with primary alcohols by a reusable Pt nanocluster catalyst
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The platinum rule: Heterogeneous, additive-free C-3 selective alkylation of indoles by aliphatic and aromatic alcohols proceeded under transfer hydrogenation conditions with the reusable Pt/θ-Al2O 3 catalyst (see scheme; TON=turnover number). Copyright
- Siddiki, S. M. A. Hakim,Kon, Kenichi,Shimizu, Ken-Ichi
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p. 14416 - 14419
(2013/11/06)
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- Transition-Metal-Catalyzed Regioselective Alkylation of Indoles with Alcohols
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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
- Putra, Anggi Eka,Takigawa, Kei,Tanaka, Hatsuki,Ito, Yoshihiko,Oe, Yohei,Ohta, Tetsuo
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p. 6344 - 6354
(2013/10/21)
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