Ethynylation of pyrroles with 1-acyl-2-bromoacetylenes on alumina: a formal ‘inverse Sonogashira coupling’
B. A. Trofimov
1
,
Zinaida V. Stepanova
1
,
Lyubov N. Sobenina
1
,
Al'bina I Mikhaleva
1
,
Igor Ushakov
1
Publication type: Journal Article
Publication date: 2004-08-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Pyrroles are cross-coupled with 1-acyl-2-bromoacetylenes on the surface of Al 2 O 3 at room temperature under solvent-free conditions to afford 2-(acylethynyl)pyrroles with 100% regioselectivity and in good yields, thus representing the first example of a palladium-, copper-, base-, and solvent-free (‘green’) ethynylation of pyrroles, which can be considered a formal ‘inverse Sonogashira coupling’. Given the interest in functionalized pyrroles and acetylenes, this new facile and environmentally friendly cross-coupling should be of significant interest for the role of acylhaloacetylenes in pyrrole and acetylene chemistry.
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113
Total citations:
113
Citations from 2025:
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(6.19%)
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GOST
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Trofimov B. A. et al. Ethynylation of pyrroles with 1-acyl-2-bromoacetylenes on alumina: a formal ‘inverse Sonogashira coupling’ // Tetrahedron Letters. 2004. Vol. 45. No. 34. pp. 6513-6516.
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Trofimov B. A., Stepanova Z. V., Sobenina L. N., Mikhaleva A. I., Ushakov I. Ethynylation of pyrroles with 1-acyl-2-bromoacetylenes on alumina: a formal ‘inverse Sonogashira coupling’ // Tetrahedron Letters. 2004. Vol. 45. No. 34. pp. 6513-6516.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1016/j.tetlet.2004.06.114
UR - https://doi.org/10.1016/j.tetlet.2004.06.114
TI - Ethynylation of pyrroles with 1-acyl-2-bromoacetylenes on alumina: a formal ‘inverse Sonogashira coupling’
T2 - Tetrahedron Letters
AU - Trofimov, B. A.
AU - Stepanova, Zinaida V.
AU - Sobenina, Lyubov N.
AU - Mikhaleva, Al'bina I
AU - Ushakov, Igor
PY - 2004
DA - 2004/08/01
PB - Elsevier
SP - 6513-6516
IS - 34
VL - 45
SN - 0040-4039
SN - 1873-3581
ER -
Cite this
BibTex (up to 50 authors)
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@article{2004_Trofimov,
author = {B. A. Trofimov and Zinaida V. Stepanova and Lyubov N. Sobenina and Al'bina I Mikhaleva and Igor Ushakov},
title = {Ethynylation of pyrroles with 1-acyl-2-bromoacetylenes on alumina: a formal ‘inverse Sonogashira coupling’},
journal = {Tetrahedron Letters},
year = {2004},
volume = {45},
publisher = {Elsevier},
month = {aug},
url = {https://doi.org/10.1016/j.tetlet.2004.06.114},
number = {34},
pages = {6513--6516},
doi = {10.1016/j.tetlet.2004.06.114}
}
Cite this
MLA
Copy
Trofimov, B. A., et al. “Ethynylation of pyrroles with 1-acyl-2-bromoacetylenes on alumina: a formal ‘inverse Sonogashira coupling’.” Tetrahedron Letters, vol. 45, no. 34, Aug. 2004, pp. 6513-6516. https://doi.org/10.1016/j.tetlet.2004.06.114.
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