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Au(I)-Catalyzed Pictet-Spengler Reactions: a Journey Around the Indole Ring

01 December 2020, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Au(I) complexes catalyze iso-Pictet-Spengler reactions. Ethylamine or methylamine chains were introduced at C2, C4 or at the nitrogen atom of the indole ring, and the corresponding substrates were reacted in the presence of aldehydes and catalytic amounts of Au(I) complexes, leading to a variety of polycyclic scaffolds. Selectivity could be achieved in the course of a double iso-Pictet-Spengler reaction involving two successive aldehydes, leading to highly complex molecules.

Keywords

Gold Catalysis
Indoles
Heterocyclic chemistry
Pictet-Spengler-type cyclization

Supplementary materials

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Now Published

Au(I)-Catalyzed Pictet–Spengler Reactions All around the Indole Ring [opens in a new tab]
Pierre Milcendeau, Zhenhao Zhang, Nicolas Glinsky-Olivier, Elsa van Elslande, Xavier Guinchard journal article
The Journal of Organic Chemistry , Volume 86, Issue 9
Online publication date: Apr 23, 2021

Version History

Dec 01, 2020 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv.13296446.v1
D O I: 10.26434/chemrxiv.13296446.v1 [opens in a new tab]

Funding

CHARMMMAT Laboratory of Excellence (ANR-11-LABX0039)
MESRI (Paris-Saclay University)
China Scholarship Council

Author’s competing interest statement

no conflict of interest

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