Synthesis of functionalized CF3-containing heterocycles via [2,3]-sigmatropic rearrangement and sequential catalytic carbocyclization
Daria V Vorobyeva
1
,
Artur K Mailyan
1
,
A. S. Peregudov
1
,
Natalia M Karimova
1
,
Tamara P Vasilyeva
1
,
Christian Bruneau
2
,
Pierre H. Dixneuf
2
,
Publication type: Journal Article
Publication date: 2011-05-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
A new efficient access to functionalized CF3-substituted and nitrogen or sulfur-containing heterocycles has been developed directly from diazocompounds CF3C(N2)Z (Z=CO2Me, P(O)(OEt)2). The method is based on the direct selective synthesis of doubly unsaturated substrates followed by metal-mediated carbocylization. The first step has been performed by Cu(II)-catalyzed [2,3]-sigmatropic rearrangement of propargyl- or/and allyl-containing sulfur and nitrogen ylides leading to fluorinated enynes, diolefins, and especially allenynes derivatives. The second step involves their carbocyclization via ring closing metathesis and Pauson-Khand reaction.
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Total citations:
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Citations from 2025:
2
(4.88%)
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GOST
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Vorobyeva D. V. et al. Synthesis of functionalized CF3-containing heterocycles via [2,3]-sigmatropic rearrangement and sequential catalytic carbocyclization // Tetrahedron. 2011. Vol. 67. No. 19. pp. 3524-3532.
GOST all authors (up to 50)
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Vorobyeva D. V., Mailyan A. K., Peregudov A. S., Karimova N. M., Vasilyeva T. P., Bushmarinov I. S., Bruneau C., Dixneuf P. H., Osipov S. N. Synthesis of functionalized CF3-containing heterocycles via [2,3]-sigmatropic rearrangement and sequential catalytic carbocyclization // Tetrahedron. 2011. Vol. 67. No. 19. pp. 3524-3532.
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RIS
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TY - JOUR
DO - 10.1016/j.tet.2011.03.031
UR - https://doi.org/10.1016/j.tet.2011.03.031
TI - Synthesis of functionalized CF3-containing heterocycles via [2,3]-sigmatropic rearrangement and sequential catalytic carbocyclization
T2 - Tetrahedron
AU - Vorobyeva, Daria V
AU - Mailyan, Artur K
AU - Peregudov, A. S.
AU - Karimova, Natalia M
AU - Vasilyeva, Tamara P
AU - Bushmarinov, I. S.
AU - Bruneau, Christian
AU - Dixneuf, Pierre H.
AU - Osipov, Sergey N
PY - 2011
DA - 2011/05/01
PB - Elsevier
SP - 3524-3532
IS - 19
VL - 67
SN - 0040-4020
SN - 1464-5416
ER -
Cite this
BibTex (up to 50 authors)
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@article{2011_Vorobyeva,
author = {Daria V Vorobyeva and Artur K Mailyan and A. S. Peregudov and Natalia M Karimova and Tamara P Vasilyeva and I. S. Bushmarinov and Christian Bruneau and Pierre H. Dixneuf and Sergey N Osipov},
title = {Synthesis of functionalized CF3-containing heterocycles via [2,3]-sigmatropic rearrangement and sequential catalytic carbocyclization},
journal = {Tetrahedron},
year = {2011},
volume = {67},
publisher = {Elsevier},
month = {may},
url = {https://doi.org/10.1016/j.tet.2011.03.031},
number = {19},
pages = {3524--3532},
doi = {10.1016/j.tet.2011.03.031}
}
Cite this
MLA
Copy
Vorobyeva, Daria V., et al. “Synthesis of functionalized CF3-containing heterocycles via [2,3]-sigmatropic rearrangement and sequential catalytic carbocyclization.” Tetrahedron, vol. 67, no. 19, May. 2011, pp. 3524-3532. https://doi.org/10.1016/j.tet.2011.03.031.
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