Palladium-Catalyzed Tsuji–Trost-Type Reaction of 3-Indolylmethylacetates with O, and S Soft Nucleophiles
Antonia Iazzetti, Antonio Arcadi, Marco Chiarini, Giancarlo Fabrizi, Antonella Goggiamani, Federico Marrone, Andrea Serraiocco, Roberta Zoppoli
TL;DR
This paper presents a new palladium-catalyzed method to synthesize indole derivatives using a readily available natural compound.
Contribution
A novel Tsuji–Trost-type reaction using indole-3-carbinol for efficient and regioselective synthesis of bioactive indoles.
Findings
The reaction shows high regioselectivity with nucleophilic substitution occurring only at the benzylic position.
The method allows appending sulfonyl units to indoles, enabling new bioactive molecule synthesis.
Abstract
The chemical valorization of widespread molecules in renewable sources is a field of research widely investigated in the last decades. In this context, we envisaged that indole-3-carbinol, present in different Cruciferae plants, could be a readily available building block for the synthesis of various classes of indoles through a palladium-catalyzed Tsuji–Trost-type reaction with O and S soft nucleophiles. The regiochemical outcome of this high-yielding functionalization shows that the nucleophilic substitution occurs only at the benzylic position. Interestingly, with this protocol, the sulfonyl unit could be appended to the indole nucleus, providing convenient access to new classes of molecules with potential bioactivity.
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Taxonomy
TopicsSynthesis of Indole Derivatives · Catalytic C–H Functionalization Methods · Catalytic Cross-Coupling Reactions