Journal of Organic Chemistry, volume 88, issue 5, pages 2869-2883
Triphenylcyclopentadienyl Rhodium Complexes in Catalytic C-H Annulations. Application for Synthesis of Natural Isocoumarins
Shutkov Ilya A.
2
,
Loginov Dmitry A.
1, 3
Publication type: Journal Article
Publication date: 2023-02-09
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
Efficient protocols for the synthesis of triphenylcyclopentadienyl rhodium halides [(1,2,4-C5Ph3H2)RhX2]2 (1a,b: X = Cl, I) starting from 1,2,4-triphenylcyclopentadiene or the cyclooctadiene derivative (1,2,4-C5Ph3H2)Rh(cod) (2) were developed. Iodide abstraction from 1b with thallium or silver salts allowed us to prepare rhodocenium [(1,2,4-C5Ph3H2)RhCp]PF6 (3PF6) and mesitylene complex [(1,2,4-C5Ph3H2)Rh(mesitylene)](SbF6)2 (4(SbF6)2). Halides 1a,b (at 0.5 mol % loading) showed high catalytic activity in the construction of C–C, C–O, and C–N bonds via the C(sp2)–H activation approach. Their efficiency was demonstrated in the synthesis of more than 40 examples of polycyclic organic compounds (such as isocoumarins and naphthalenes, as well as isoquinolinium and dibenzo[a,f]quinolizinium salts). The protocols developed tolerate a wide range of functional groups. In particular, they were successfully used for the atom- and step-economical synthesis of hydroxy-substituted isocoumarins, including the natural product oospalactone 7fe. The 6- or 8-hydroxy-substituted isocoumarins showed moderate antiproliferative activity against several human cell lines in vitro.
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Kharitonov V. B. et al. Triphenylcyclopentadienyl Rhodium Complexes in Catalytic C-H Annulations. Application for Synthesis of Natural Isocoumarins // Journal of Organic Chemistry. 2023. Vol. 88. No. 5. pp. 2869-2883.
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Kharitonov V. B., Muratov D. V., Nelyubina Y. V., Shutkov I. A., Nazarov A. A., Loginov D. A. Triphenylcyclopentadienyl Rhodium Complexes in Catalytic C-H Annulations. Application for Synthesis of Natural Isocoumarins // Journal of Organic Chemistry. 2023. Vol. 88. No. 5. pp. 2869-2883.
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TY - JOUR
DO - 10.1021/acs.joc.2c02526
UR - https://doi.org/10.1021%2Facs.joc.2c02526
TI - Triphenylcyclopentadienyl Rhodium Complexes in Catalytic C-H Annulations. Application for Synthesis of Natural Isocoumarins
T2 - Journal of Organic Chemistry
AU - Kharitonov, Vladimir B.
AU - Muratov, Dmitry V.
AU - Nelyubina, Yulia V.
AU - Shutkov, Ilya A.
AU - Nazarov, Alexey A.
AU - Loginov, Dmitry A.
PY - 2023
DA - 2023/02/09 00:00:00
PB - American Chemical Society (ACS)
SP - 2869-2883
IS - 5
VL - 88
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2023_Kharitonov,
author = {Vladimir B. Kharitonov and Dmitry V. Muratov and Yulia V. Nelyubina and Ilya A. Shutkov and Alexey A. Nazarov and Dmitry A. Loginov},
title = {Triphenylcyclopentadienyl Rhodium Complexes in Catalytic C-H Annulations. Application for Synthesis of Natural Isocoumarins},
journal = {Journal of Organic Chemistry},
year = {2023},
volume = {88},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021%2Facs.joc.2c02526},
number = {5},
pages = {2869--2883},
doi = {10.1021/acs.joc.2c02526}
}
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Kharitonov, Vladimir B., et al. “Triphenylcyclopentadienyl Rhodium Complexes in Catalytic C-H Annulations. Application for Synthesis of Natural Isocoumarins.” Journal of Organic Chemistry, vol. 88, no. 5, Feb. 2023, pp. 2869-2883. https://doi.org/10.1021%2Facs.joc.2c02526.