CuI-catalyzed highly regioselective CH functionalization of indoles using indole-3-tosylhydrazones as carbene precursor: An efficient synthesis of 3,3-bis(indolyl)methane derivatives

[Display omitted] •Synthesis of bis-indole derivatives having no substitution on methylene-bridge.•Copper-catalyzed carbene insertion reactions.•Highly regioselective C-3 functionalization of indole over the C-1 and N-1 positions.•Gram scale synthesis of bis-indole derivatives. Herein, we have devel...

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Bibliographic Details
Published in:Tetrahedron letters 2019-10, Vol.60 (43), Article 151162
Main Authors: Kamboj, Priya, Dutt, Sunil, Chakroborty, Sourav, Tyagi, Vikas
Format: Article
Language:English
Subjects:
Bis indoles
Carbene insertion
Copper-catalyst
N-tosylhydrazone
Regioselective
Online Access:Get full text
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Summary:[Display omitted] •Synthesis of bis-indole derivatives having no substitution on methylene-bridge.•Copper-catalyzed carbene insertion reactions.•Highly regioselective C-3 functionalization of indole over the C-1 and N-1 positions.•Gram scale synthesis of bis-indole derivatives. Herein, we have developed a novel approach for synthesizing symmetrical and unsymmetrical 3,3-bis(indolyl)methane derivatives via CuI-catalyzed CH functionalization of indole using indole-3-tosylhydrazones as carbene precursor. This procedure works well with different substitutions such as NO2, Br, CH3 and OMe on indole or indole-3-tosylhydrazones and features high regioselectivity for C-3 functionalization over the C-1 and N-1 positions. Further, we have also revealed the feasibility of this protocol in a one-pot fashion starting from indole-3-carboxyaldehyde.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.151162