Nickel-catalysed chemoselective C-3 alkylation of indoles with alcohols through a borrowing hydrogen method

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...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 56; no. 98; pp. 15442 - 15445
Main Authors Bains, Amreen K, Biswas, Ayanangshu, Adhikari, Debashis
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.12.2020
Royal Society of Chemistry
Subjects
Alcohol
Alcohols
Alkylation
Chemistry
Chemistry, Multidisciplinary
Ethanol
Indoles
Nickel
NMR
Nuclear magnetic resonance
Physical Sciences
Science & Technology
FUNCTIONALIZATION
OXINDOLE
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Summary: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. A nickel catalysed chemoselective C3-alkylation of indole is reported that follows a borrowing hydrogen method promoted by a radical.
Bibliography:10.1039/d0cc07169b
Electronic supplementary information (ESI) available: Detailed synthetic procedure, control experiments, characterization details, NMR spectra. See DOI
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc07169b