Synthesis of Carbazoles by a Diverted Bischler-Napieralski Cascade Reaction

Matteo Faltracco; Said Ortega-Rosales; Elwin Janssen; Rǎzvan C. Cioc; Christophe M.L. Vande Velde; Eelco Ruijter

doi:10.1021/acs.orglett.1c00785

Synthesis of Carbazoles by a Diverted Bischler-Napieralski Cascade Reaction

Matteo Faltracco, Said Ortega-Rosales, Elwin Janssen, Rǎzvan C. Cioc, Christophe M.L. Vande Velde, Eelco Ruijter^*

^*Corresponding author for this work

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

An unforeseen twist in a seemingly trivial Bischler-Napieralski reaction led to the selective formation of an unexpected carbazole product. The reaction proved to be general, providing access to a range of diversely substituted carbazoles from readily available substrates. Judicious variation of substituents revealed a complex cascade mechanism comprising no less than 10 elementary steps, that could be diverted in multiple ways toward various other carbazole derivatives.

Original language	English
Pages (from-to)	3100-3104
Number of pages	5
Journal	Organic letters
Volume	23
Issue number	8
Early online date	31 Mar 2021
DOIs	https://doi.org/10.1021/acs.orglett.1c00785
Publication status	Published - 16 Apr 2021

Bibliographical note

Funding Information:
This work was financially supported by The Netherlands Organisation for Scientific Research (NWO).We thank Xander Schaapkens and Ad Ruigrok van de Werve for preliminary experiments and Daniël Preschel for HRMS measurements (all VUA). We thank the Hercules Foundation (Project AUGE/11/029 “3D-SPACE: 3D Structural Platform Aiming for Chemical Excellence”) for funding the diffractometer, and Prof. Kristof Van Hecke (University of Ghent) for making available diffractometer time.

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

Copyright:
Copyright 2021 Elsevier B.V., All rights reserved.

Access to Document

10.1021/acs.orglett.1c00785

Persistent URL (handle)

Copy link address

Cite this

@article{4589daf70dae4bda9257d53727e07b34,

title = "Synthesis of Carbazoles by a Diverted Bischler-Napieralski Cascade Reaction",

abstract = "An unforeseen twist in a seemingly trivial Bischler-Napieralski reaction led to the selective formation of an unexpected carbazole product. The reaction proved to be general, providing access to a range of diversely substituted carbazoles from readily available substrates. Judicious variation of substituents revealed a complex cascade mechanism comprising no less than 10 elementary steps, that could be diverted in multiple ways toward various other carbazole derivatives. ",

author = "Matteo Faltracco and Said Ortega-Rosales and Elwin Janssen and Cioc, {Rǎzvan C.} and {Vande Velde}, {Christophe M.L.} and Eelco Ruijter",

note = "Funding Information: This work was financially supported by The Netherlands Organisation for Scientific Research (NWO).We thank Xander Schaapkens and Ad Ruigrok van de Werve for preliminary experiments and Dani{\"e}l Preschel for HRMS measurements (all VUA). We thank the Hercules Foundation (Project AUGE/11/029 “3D-SPACE: 3D Structural Platform Aiming for Chemical Excellence”) for funding the diffractometer, and Prof. Kristof Van Hecke (University of Ghent) for making available diffractometer time. Publisher Copyright: {\textcopyright} 2021 The Authors. Published by American Chemical Society. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",

year = "2021",

month = apr,

day = "16",

doi = "10.1021/acs.orglett.1c00785",

language = "English",

volume = "23",

pages = "3100--3104",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - Synthesis of Carbazoles by a Diverted Bischler-Napieralski Cascade Reaction

AU - Faltracco, Matteo

AU - Ortega-Rosales, Said

AU - Janssen, Elwin

AU - Cioc, Rǎzvan C.

AU - Vande Velde, Christophe M.L.

AU - Ruijter, Eelco

N1 - Funding Information: This work was financially supported by The Netherlands Organisation for Scientific Research (NWO).We thank Xander Schaapkens and Ad Ruigrok van de Werve for preliminary experiments and Daniël Preschel for HRMS measurements (all VUA). We thank the Hercules Foundation (Project AUGE/11/029 “3D-SPACE: 3D Structural Platform Aiming for Chemical Excellence”) for funding the diffractometer, and Prof. Kristof Van Hecke (University of Ghent) for making available diffractometer time. Publisher Copyright: © 2021 The Authors. Published by American Chemical Society. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2021/4/16

Y1 - 2021/4/16

N2 - An unforeseen twist in a seemingly trivial Bischler-Napieralski reaction led to the selective formation of an unexpected carbazole product. The reaction proved to be general, providing access to a range of diversely substituted carbazoles from readily available substrates. Judicious variation of substituents revealed a complex cascade mechanism comprising no less than 10 elementary steps, that could be diverted in multiple ways toward various other carbazole derivatives.

AB - An unforeseen twist in a seemingly trivial Bischler-Napieralski reaction led to the selective formation of an unexpected carbazole product. The reaction proved to be general, providing access to a range of diversely substituted carbazoles from readily available substrates. Judicious variation of substituents revealed a complex cascade mechanism comprising no less than 10 elementary steps, that could be diverted in multiple ways toward various other carbazole derivatives.

UR - http://www.scopus.com/inward/record.url?scp=85104899839&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85104899839&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.1c00785

DO - 10.1021/acs.orglett.1c00785

M3 - Article

C2 - 33787266

AN - SCOPUS:85104899839

SN - 1523-7060

VL - 23

SP - 3100

EP - 3104

JO - Organic letters

JF - Organic letters

IS - 8

ER -

Synthesis of Carbazoles by a Diverted Bischler-Napieralski Cascade Reaction

Abstract

Bibliographical note

Access to Document

Persistent URL (handle)

Other files and links

Fingerprint

CCDC 2062984: Experimental Crystal Structure Determination

Cite this

Synthesis of Carbazoles by a Diverted Bischler-Napieralski Cascade Reaction

Abstract

Bibliographical note

Access to Document

Persistent URL (handle)

Other files and links

Fingerprint

Datasets

CCDC 2062984: Experimental Crystal Structure Determination

Cite this