Home / Publications / Aluminium oxide-mediated cross-coupling of pyrroles with 1-bromo-2-(trifluoroacetyl)acetylene: a quantum-chemical insight

Aluminium oxide-mediated cross-coupling of pyrroles with 1-bromo-2-(trifluoroacetyl)acetylene: a quantum-chemical insight

Denis Nikolaevich Tomilin 1
Denis Nikolaevich Tomilin
, 
Dmitri Yul'evich Soshnikov 1, 2
Dmitri Yul'evich Soshnikov
, 
Alexander Borisovich Trofimov 2
Alexander Borisovich Trofimov
, 
Maxim Dmitrievich Gotsko 1
Maxim Dmitrievich Gotsko
,  , 
Igor Alekseevich Ushakov 1
Igor Alekseevich Ushakov
, 
Andrei Valer'evich Afonin 1
Andrei Valer'evich Afonin
, 
Andrei Borisovich Koldobskii 3
Andrei Borisovich Koldobskii
, 
Nadezhda Moiseevna Vitkovskaya 2
Nadezhda Moiseevna Vitkovskaya
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2016.11.006
Published 2016-10-27
Communication , Volume 26, Issue 6, 480-482
11
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Tomilin D. N. et al. Aluminium oxide-mediated cross-coupling of pyrroles with 1-bromo-2-(trifluoroacetyl)acetylene: a quantum-chemical insight // Mendeleev Communications. 2016. Vol. 26. No. 6. pp. 480-482.
GOST all authors (up to 50) Copy
Tomilin D. N., Soshnikov D. Y., Trofimov A. B., Gotsko M. D., Sobenina L. N., Ushakov I. A., Afonin A. V., Koldobskii A. B., Vitkovskaya N. M., Trofimov B. A. Aluminium oxide-mediated cross-coupling of pyrroles with 1-bromo-2-(trifluoroacetyl)acetylene: a quantum-chemical insight // Mendeleev Communications. 2016. Vol. 26. No. 6. pp. 480-482.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2016.11.006
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.11.006
TI - Aluminium oxide-mediated cross-coupling of pyrroles with 1-bromo-2-(trifluoroacetyl)acetylene: a quantum-chemical insight
T2 - Mendeleev Communications
AU - Tomilin, Denis Nikolaevich
AU - Soshnikov, Dmitri Yul'evich
AU - Trofimov, Alexander Borisovich
AU - Gotsko, Maxim Dmitrievich
AU - Sobenina, Lyubov Nikolaevna
AU - Ushakov, Igor Alekseevich
AU - Afonin, Andrei Valer'evich
AU - Koldobskii, Andrei Borisovich
AU - Vitkovskaya, Nadezhda Moiseevna
AU - Trofimov, Boris Aleksandrovich
PY - 2016
DA - 2016/10/27
PB - Mendeleev Communications
SP - 480-482
IS - 6
VL - 26
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2016_Tomilin,
author = {Denis Nikolaevich Tomilin and Dmitri Yul'evich Soshnikov and Alexander Borisovich Trofimov and Maxim Dmitrievich Gotsko and Lyubov Nikolaevna Sobenina and Igor Alekseevich Ushakov and Andrei Valer'evich Afonin and Andrei Borisovich Koldobskii and Nadezhda Moiseevna Vitkovskaya and Boris Aleksandrovich Trofimov},
title = {Aluminium oxide-mediated cross-coupling of pyrroles with 1-bromo-2-(trifluoroacetyl)acetylene: a quantum-chemical insight},
journal = {Mendeleev Communications},
year = {2016},
volume = {26},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.11.006},
number = {6},
pages = {480--482},
doi = {10.1016/j.mencom.2016.11.006}
}
MLA
Cite this
MLA Copy
Tomilin, Denis Nikolaevich, et al. “Aluminium oxide-mediated cross-coupling of pyrroles with 1-bromo-2-(trifluoroacetyl)acetylene: a quantum-chemical insight.” Mendeleev Communications, vol. 26, no. 6, Oct. 2016, pp. 480-482. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.11.006.

Abstract

Cross-coupling of NH-pyrroles with 1-bromo-2-(trifluoroacetyl) acetylene in the Al2O3 medium affords (E)-4-bromo-1,1,1-trifluoro-4-(pyrrol-2-yl)but-3-en-2-ones instead of the expected 2-ethynylated products. Quantum-chemical analysis shows strong intramolecular hydrogen bonding between NH and trifluoroacetyl groups, higher NH acidity and deeper charge transfer to the ethenyl moiety, which determines the reaction pathway.

References

1.
Ethynylation of pyrroles with 1-acyl-2-bromoacetylenes on alumina: a formal ‘inverse Sonogashira coupling’
Trofimov B.A., Stepanova Z.V., Sobenina L.N., Mikhaleva A.I., Ushakov I.A.
Tetrahedron Letters, 2004
2.
Trofimov B.A., Stepanova Z.V., Sobenina L.N., Mikhaleva A.I., Sinegovskaya L.M., Potekhin K.A., Fedyanin I.V.
Mendeleev Communications, 2005
3.
Ethynylation of indoles with 1-benzoyl-2-bromoacetylene on Al2O3
Sobenina L.N., Demenev A.P., Mikhaleva A.I., Ushakov I.A., Vasil’tsov A.M., Ivanov A.V., Trofimov B.A.
Tetrahedron Letters, 2006
4.
Reaction of indoles with ethyl bromopropynoate over Al2O3 surface
Petrova O.V., Sobenina L.N., Ushakov I.A., Mikhaleva A.I.
Russian Journal of Organic Chemistry, 2008
5.
10.1016/j.mencom.2016.11.006_bib0025
Trofimov
Chemistry of Pyrroles, 2014
6.
10.1016/j.mencom.2016.11.006_bib0030
Trofimov
2009
7.
C-Ethynylpyrroles: synthesis and reactivity
Sobenina L.N., Tomilin D.N., Trofimov B.A.
Russian Chemical Reviews, 2014
8.
Topochemical mechanoactivated phosphonylethynylation of pyrroles with chloroethynylphosphonates on solid Al2O3 or K2CO3 media
Gotsko M.D., Sobenina L.N., Tomilin D.N., Ushakov I.A., Dogadina A.V., Trofimov B.A.
Tetrahedron Letters, 2015
9.
Direct synthesis of butadiynyl-substituted pyrroles under solvent- and transition metal-free conditions
Tomilin D.N., Pigulski B., Gulia N., Arendt A., Sobenina L.N., Mikhaleva A.I., Szafert S., Trofimov B.A.
RSC Advances, 2015
10.
Convenient synthesis of methyl indol-2-ylpropiolate
Passarella D., Lesma G., Deleo M., Martinelli M., Silvani A.
Journal of the Chemical Society Perkin Transactions 1, 1999
11.
2-Halopyrroles. Synthesis and chemistry
Cordell G.A.
Journal of Organic Chemistry, 1975
12.
10.1016/j.mencom.2016.11.006_bib0060
Bird
1984