A chemo- and regioselective tandem [3+2]heteroannulation strategy for carbazole synthesis: combining two mechanistically distinct bond-forming processes

Emma Campbell; Andrea Taladriz-Sender; Olivia I. Paisley; Alan R. Kennedy; Jacob T. Bush; Glenn A. Burley

doi:10.1021/acs.joc.1c02943

A chemo- and regioselective tandem [3+2]heteroannulation strategy for carbazole synthesis: combining two mechanistically distinct bond-forming processes

Emma Campbell, Andrea Taladriz-Sender, Olivia I. Paisley, Alan R. Kennedy, Jacob T. Bush, Glenn A. Burley

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

31 Downloads (Pure)

Abstract

A modular approach to prepare tri- and tetracyclic carbazoles by a sequential [3 + 2]heteroannulation is described. First, optimization of Pd-catalyzed Buchwald-Hartwig amination followed by C/N-arylation in a one-pot process is established. Second, mechanistic analyses identified the origins of chemo- and regioselective sequential control of both bond-forming steps. Finally, the substrate scope is demonstrated by the preparation of a range of tri- and tetracyclic carbazoles, including expedient access to several natural products and anti-cancer agents.

Original language	English
Pages (from-to)	4603-4616
Number of pages	14
Journal	Journal of Organic Chemistry
Volume	87
Issue number	7
Early online date	18 Mar 2022
DOIs	https://doi.org/10.1021/acs.joc.1c02943
Publication status	Published - 1 Apr 2022

Keywords

carbazoles
Buchwald–Hartwig amination
anti-cancer agents

UN SDGs

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

Access to Document

10.1021/acs.joc.1c02943Licence: CC BY 4.0

Campbell-etal-JOC-2022-A-chemo-and-regioselective-tandem-heteroannulation-strategy-for-carbazole-synthesisFinal published version, 1.62 MBLicence: CC BY 4.0

1 Finished

Regulation of alternative splicing by G-quadruplexes: molecular mechanisms and tools to manipulate gene expression
Burley, G. (Principal Investigator)
BBSRC (Biotech & Biological Sciences Research Council)
1/05/18 → 28/04/21
Project: Research

Data for: "A Chemo- and Regioselective Tandem [3+2]Heteroannulation Strategy for Carbazole Synthesis: Synergizing Two Mechanistically Distinct Bond-Forming Processes"
Taladriz Sender, A. (Creator), Campbell, E. (Creator), Rutherford, O. (Contributor), Kennedy, A. (Contributor), Burley, G. (Creator) & Bush, J. (Contributor), University of Strathclyde, 17 Mar 2022
DOI: 10.15129/f45b6f45-b8f7-435a-b5a3-097e3ff7397c, https://pubs.acs.org/doi/10.1021/acs.joc.1c02943
Dataset

3 Citations
1 Book/Film/Article review

Splice-switching small molecules: a new therapeutic approach to modulate gene expression
Taladriz-Sender, A., Campbell, E. & Burley, G. A., 1 Sept 2019, In: Methods. 167, p. 134-142 9 p.
Research output: Contribution to journal › Book/Film/Article review › peer-review

Open Access
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8 Citations (Scopus)

51 Downloads (Pure)

1 Invited talk

Invited talk
Burley, G. (Speaker)
14 Jun 2022
Activity: Talk or presentation types › Invited talk

Cite this

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title = "A chemo- and regioselective tandem [3+2]heteroannulation strategy for carbazole synthesis: combining two mechanistically distinct bond-forming processes",

abstract = "A modular approach to prepare tri- and tetracyclic carbazoles by a sequential [3 + 2]heteroannulation is described. First, optimization of Pd-catalyzed Buchwald-Hartwig amination followed by C/N-arylation in a one-pot process is established. Second, mechanistic analyses identified the origins of chemo- and regioselective sequential control of both bond-forming steps. Finally, the substrate scope is demonstrated by the preparation of a range of tri- and tetracyclic carbazoles, including expedient access to several natural products and anti-cancer agents.",

keywords = "carbazoles, Buchwald–Hartwig amination, anti-cancer agents",

author = "Emma Campbell and Andrea Taladriz-Sender and Paisley, {Olivia I.} and Kennedy, {Alan R.} and Bush, {Jacob T.} and Burley, {Glenn A.}",

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T2 - combining two mechanistically distinct bond-forming processes

AU - Campbell, Emma

AU - Taladriz-Sender, Andrea

AU - Paisley, Olivia I.

AU - Kennedy, Alan R.

AU - Bush, Jacob T.

AU - Burley, Glenn A.

PY - 2022/4/1

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N2 - A modular approach to prepare tri- and tetracyclic carbazoles by a sequential [3 + 2]heteroannulation is described. First, optimization of Pd-catalyzed Buchwald-Hartwig amination followed by C/N-arylation in a one-pot process is established. Second, mechanistic analyses identified the origins of chemo- and regioselective sequential control of both bond-forming steps. Finally, the substrate scope is demonstrated by the preparation of a range of tri- and tetracyclic carbazoles, including expedient access to several natural products and anti-cancer agents.

AB - A modular approach to prepare tri- and tetracyclic carbazoles by a sequential [3 + 2]heteroannulation is described. First, optimization of Pd-catalyzed Buchwald-Hartwig amination followed by C/N-arylation in a one-pot process is established. Second, mechanistic analyses identified the origins of chemo- and regioselective sequential control of both bond-forming steps. Finally, the substrate scope is demonstrated by the preparation of a range of tri- and tetracyclic carbazoles, including expedient access to several natural products and anti-cancer agents.

KW - carbazoles

KW - Buchwald–Hartwig amination

KW - anti-cancer agents

U2 - 10.1021/acs.joc.1c02943

DO - 10.1021/acs.joc.1c02943

M3 - Article

SN - 0022-3263

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 7

ER -

A chemo- and regioselective tandem [3+2]heteroannulation strategy for carbazole synthesis: combining two mechanistically distinct bond-forming processes

Abstract

Keywords

UN SDGs

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Projects

Regulation of alternative splicing by G-quadruplexes: molecular mechanisms and tools to manipulate gene expression

Datasets

Data for: "A Chemo- and Regioselective Tandem [3+2]Heteroannulation Strategy for Carbazole Synthesis: Synergizing Two Mechanistically Distinct Bond-Forming Processes"

Research output

Splice-switching small molecules: a new therapeutic approach to modulate gene expression

Activities

Invited talk

Cite this