Synthesis of Carbazoles and Dihydrocarbazoles by a Divergent Cascade Reaction of Donor-Acceptor Cyclopropanes

Matteo Faltracco, Matteo Damian, Eelco Ruijter*

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

An alkylation/olefination cascade of indolecarboxaldehydes and phosphonate-functionalized donor-acceptor cyclopropanes affords functionalized dihydrocarbazoles and cyclohepta[cd]indoles in formal (3 + 3) and (4 + 3) cycloadditions. A minor modification to the reaction conditions also allows access to the fully aromatic heterocyclic scaffolds by thermal loss of an electron-rich aryl moiety.

Original languageEnglish
Pages (from-to)7592-7596
Number of pages5
JournalOrganic letters
Volume23
Issue number19
Early online date20 Sept 2021
DOIs
Publication statusPublished - 1 Oct 2021

Bibliographical note

Funding Information:
This work was financially supported by The Netherlands Organisation for Scientific Research (NWO). We thank Elwin Janssen for NMR support and Daniël Preschel for HRMS measurements.

Publisher Copyright:
© 2021 The Authors. Published by American Chemical Society.

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