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