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.

Funding

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.

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