Synthesis of Pyrrolo[2,1-a]isoquinolinium Salts from 1-Pyrrolines and Alkynes via Rhodium-Catalyzed C–H Functionalization/N-Annulation Tandem Reaction
Publication type: Journal Article
Publication date: 2022-05-04
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
35507755
Organic Chemistry
Abstract
A convenient synthesis of pyrrolo[2,1-a]isoquinolinium salts from 1-pyrrolines and alkynes through rhodium-catalyzed C-H functionalization/N-annulation tandem reaction is described. The protocol features a good substrate tolerance, mild reaction conditions, and high yields of target products. Exploration of the alkyne scope unexpectedly revealed a novel labile functional group-promoted rhodium-catalyzed C-H functionalization/C-annulation/elimination cascade reaction of 1-pyrrolines with electron-deficient alkynes.
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12
Total citations:
12
Citations from 2024:
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(16%)
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GOST
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Shabalin D. A. et al. Synthesis of Pyrrolo[2,1-a]isoquinolinium Salts from 1-Pyrrolines and Alkynes via Rhodium-Catalyzed C–H Functionalization/N-Annulation Tandem Reaction // Journal of Organic Chemistry. 2022. Vol. 87. No. 10. pp. 6860-6869.
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Shabalin D. A., Kazak M. K., Ushakov I. A., Vashchenko A. V., Schmidt E. Y. Synthesis of Pyrrolo[2,1-a]isoquinolinium Salts from 1-Pyrrolines and Alkynes via Rhodium-Catalyzed C–H Functionalization/N-Annulation Tandem Reaction // Journal of Organic Chemistry. 2022. Vol. 87. No. 10. pp. 6860-6869.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.2c00555
UR - https://doi.org/10.1021/acs.joc.2c00555
TI - Synthesis of Pyrrolo[2,1-a]isoquinolinium Salts from 1-Pyrrolines and Alkynes via Rhodium-Catalyzed C–H Functionalization/N-Annulation Tandem Reaction
T2 - Journal of Organic Chemistry
AU - Shabalin, Dmitrii A.
AU - Kazak, Maxim K
AU - Ushakov, Igor A.
AU - Vashchenko, Alexander V.
AU - Schmidt, Elena Yu.
PY - 2022
DA - 2022/05/04
PB - American Chemical Society (ACS)
SP - 6860-6869
IS - 10
VL - 87
PMID - 35507755
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2022_Shabalin,
author = {Dmitrii A. Shabalin and Maxim K Kazak and Igor A. Ushakov and Alexander V. Vashchenko and Elena Yu. Schmidt},
title = {Synthesis of Pyrrolo[2,1-a]isoquinolinium Salts from 1-Pyrrolines and Alkynes via Rhodium-Catalyzed C–H Functionalization/N-Annulation Tandem Reaction},
journal = {Journal of Organic Chemistry},
year = {2022},
volume = {87},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/acs.joc.2c00555},
number = {10},
pages = {6860--6869},
doi = {10.1021/acs.joc.2c00555}
}
Cite this
MLA
Copy
Shabalin, Dmitrii A., et al. “Synthesis of Pyrrolo[2,1-a]isoquinolinium Salts from 1-Pyrrolines and Alkynes via Rhodium-Catalyzed C–H Functionalization/N-Annulation Tandem Reaction.” Journal of Organic Chemistry, vol. 87, no. 10, May. 2022, pp. 6860-6869. https://doi.org/10.1021/acs.joc.2c00555.
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