Issue 46, 2024

Synthesis of bis(indolyl)methanes using N-heterocyclic carbene salt as a C1 precursor

Abstract

We herein describe an alkylation reaction of indoles with NHC salts to access bis(indolyl)methanes as product. The NHC salt (or free NHC) serves as a C1 precursor due to decomposition of its N-heterocyclic ring. Although the exact roles of zinc powder and acetic/formic acid remain elusive, both of them are indispensable for this reaction. Two possible reaction pathways are proposed based on the results of mechanistic experiments.

Graphical abstract: Synthesis of bis(indolyl)methanes using N-heterocyclic carbene salt as a C1 precursor

Supplementary files

Article information

Article type
Communication
Submitted
26 Sep 2024
Accepted
08 Oct 2024
First published
08 Oct 2024

Org. Biomol. Chem., 2024,22, 9058-9062

Synthesis of bis(indolyl)methanes using N-heterocyclic carbene salt as a C1 precursor

B. Zhou, Z. Gao, Y. Yang and Y. Hu, Org. Biomol. Chem., 2024, 22, 9058 DOI: 10.1039/D4OB01568A

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