Transition Metal-Free Synthesis of meta-Bromo- and meta-Trifluoromethylanilines from Cyclopentanones by a Cascade Reaction

Research output: Contribution to journal › Journal article › Research › peer-review

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Transition Metal-Free Synthesis of meta-Bromo- and meta-Trifluoromethylanilines from Cyclopentanones by a Cascade Reaction. / Staudt, Markus; Cetin, Adnan; Bunch, Lennart.

In: Chemistry: A European Journal, Vol. 28, No. 10, 202102998, 2022.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Staudt, M, Cetin, A & Bunch, L 2022, 'Transition Metal-Free Synthesis of meta-Bromo- and meta-Trifluoromethylanilines from Cyclopentanones by a Cascade Reaction', Chemistry: A European Journal, vol. 28, no. 10, 202102998. https://doi.org/10.1002/chem.202102998

APA

Staudt, M., Cetin, A., & Bunch, L. (2022). Transition Metal-Free Synthesis of meta-Bromo- and meta-Trifluoromethylanilines from Cyclopentanones by a Cascade Reaction. Chemistry: A European Journal, 28(10), [202102998]. https://doi.org/10.1002/chem.202102998

Vancouver

Staudt M, Cetin A, Bunch L. Transition Metal-Free Synthesis of meta-Bromo- and meta-Trifluoromethylanilines from Cyclopentanones by a Cascade Reaction. Chemistry: A European Journal. 2022;28(10). 202102998. https://doi.org/10.1002/chem.202102998

Author

Staudt, Markus ; Cetin, Adnan ; Bunch, Lennart. / Transition Metal-Free Synthesis of meta-Bromo- and meta-Trifluoromethylanilines from Cyclopentanones by a Cascade Reaction. In: Chemistry: A European Journal. 2022 ; Vol. 28, No. 10.

Bibtex

@article{ae5f7d7402264f65862519891e77603f,
title = "Transition Metal-Free Synthesis of meta-Bromo- and meta-Trifluoromethylanilines from Cyclopentanones by a Cascade Reaction",
abstract = "Anilines are key constituents in biologically active compounds and often obtained from transition metal-catalyzed coupling of an aryl halide with an amine. In this work, we report a transition metal-free method for the synthesis of meta-bromo- and meta-trifluoromethylanilines starting from 3-tribromomethylcyclopentanone or 3-(2-bromo-2-chloro-1,1,1-trifluoroethyl)cyclopentanone, respectively. The scope of the transformation is shown by application of primary, secondary and aromatic amines. The reaction proceeds in acceptable to high yields (20-81 %), and allows for the synthesis of anilines with substitution patterns otherwise difficult to access.",
keywords = "anilines, drug synthesis, electrocyclic ring-opening, new methodology, transition metal-free",
author = "Markus Staudt and Adnan Cetin and Lennart Bunch",
year = "2022",
doi = "10.1002/chem.202102998",
language = "English",
volume = "28",
journal = "Chemistry: A European Journal",
issn = "0947-6539",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "10",

}

RIS

TY - JOUR

T1 - Transition Metal-Free Synthesis of meta-Bromo- and meta-Trifluoromethylanilines from Cyclopentanones by a Cascade Reaction

AU - Staudt, Markus

AU - Cetin, Adnan

AU - Bunch, Lennart

PY - 2022

Y1 - 2022

N2 - Anilines are key constituents in biologically active compounds and often obtained from transition metal-catalyzed coupling of an aryl halide with an amine. In this work, we report a transition metal-free method for the synthesis of meta-bromo- and meta-trifluoromethylanilines starting from 3-tribromomethylcyclopentanone or 3-(2-bromo-2-chloro-1,1,1-trifluoroethyl)cyclopentanone, respectively. The scope of the transformation is shown by application of primary, secondary and aromatic amines. The reaction proceeds in acceptable to high yields (20-81 %), and allows for the synthesis of anilines with substitution patterns otherwise difficult to access.

AB - Anilines are key constituents in biologically active compounds and often obtained from transition metal-catalyzed coupling of an aryl halide with an amine. In this work, we report a transition metal-free method for the synthesis of meta-bromo- and meta-trifluoromethylanilines starting from 3-tribromomethylcyclopentanone or 3-(2-bromo-2-chloro-1,1,1-trifluoroethyl)cyclopentanone, respectively. The scope of the transformation is shown by application of primary, secondary and aromatic amines. The reaction proceeds in acceptable to high yields (20-81 %), and allows for the synthesis of anilines with substitution patterns otherwise difficult to access.

KW - anilines

KW - drug synthesis

KW - electrocyclic ring-opening

KW - new methodology

KW - transition metal-free

U2 - 10.1002/chem.202102998

DO - 10.1002/chem.202102998

M3 - Journal article

C2 - 35076996

VL - 28

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

SN - 0947-6539

IS - 10

M1 - 202102998

ER -

ID: 293382078