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

Matteo Faltracco; Matteo Damian; Eelco Ruijter

doi:10.1021/acs.orglett.1c02795

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 Journal › Article › Academic › peer-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 language	English
Pages (from-to)	7592-7596
Number of pages	5
Journal	Organic letters
Volume	23
Issue number	19
Early online date	20 Sept 2021
DOIs	https://doi.org/10.1021/acs.orglett.1c02795
Publication status	Published - 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.

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1021/acs.orglett.1c02795

Persistent URL (handle)

Persistent link

Cite this

@article{6c4062683b964be8b3c0e732f3de1fe2,

title = "Synthesis of Carbazoles and Dihydrocarbazoles by a Divergent Cascade Reaction of Donor-Acceptor Cyclopropanes",

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. ",

author = "Matteo Faltracco and Matteo Damian and Eelco Ruijter",

note = "Funding Information: This work was financially supported by The Netherlands Organisation for Scientific Research (NWO). We thank Elwin Janssen for NMR support and Dani{\"e}l Preschel for HRMS measurements. Publisher Copyright: {\textcopyright} 2021 The Authors. Published by American Chemical Society.",

year = "2021",

month = oct,

day = "1",

doi = "10.1021/acs.orglett.1c02795",

language = "English",

volume = "23",

pages = "7592--7596",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - Synthesis of Carbazoles and Dihydrocarbazoles by a Divergent Cascade Reaction of Donor-Acceptor Cyclopropanes

AU - Faltracco, Matteo

AU - Damian, Matteo

AU - Ruijter, Eelco

N1 - 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.

PY - 2021/10/1

Y1 - 2021/10/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85116519214&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85116519214&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.1c02795

DO - 10.1021/acs.orglett.1c02795

M3 - Article

C2 - 34543040

SN - 1523-7060

VL - 23

SP - 7592

EP - 7596

JO - Organic letters

JF - Organic letters

IS - 19

ER -

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

Abstract

Bibliographical note

UN SDGs

Access to Document

Persistent URL (handle)

Other files and links

Fingerprint

Cite this