Palladium-ADC complexes as efficient catalysts in copper-free and room temperature Sonogashira coupling
Elena A Valishina
1, 2
,
M. A. Salgueiro da Silva
1, 3
,
M. A. Kinzhalov
4
,
Svetlana A Timofeeva
4
,
Tatyana M Buslaeva
2
,
Matti Haukka
5
,
Publication type: Journal Article
Publication date: 2014-12-01
SJR: —
CiteScore: —
Impact factor: —
ISSN: 13811169
Catalysis
Physical and Theoretical Chemistry
Process Chemistry and Technology
Abstract
The metal-mediated coupling between cis-[PdCl2(CNR1)2] [R1 = cyclohexyl (Cy) 1, t-Bu 2, 2,6-Me2C6H3 (Xyl) 3, 2-Cl-6-MeC6H3 4] and hydrazones H2NN CR2R3 [R2, R3 = Ph 5; R2, R3 = C6H4(OMe-4) 6; R2/R3 = 9-fluorenyl 7; R2 = H, R3 = C6H4(OH-2) 8] provided carbene complexes cis-[PdCl2{C(N(H)N CR2R3) N(H)R1}(CNR1)] (9–24) in good (80–85%) yields. Complexes 9–24 showed high activity [yields up to 99%, and turnover numbers (TONs) up to 3.7 × 104] in the Sonogashira coupling of various aryl iodides with a range of substituted aromatic alkynes without the need of copper co-catalyst. The catalytic procedure runs at 80 °C for 1 h in EtOH using K2CO3 as a base. No formation of homocoupling or acetylene decomposition products was observed. Designed copper-free Sonogashira system can also run at room temperature giving target products with yields up to 87% and TONs up to 87.
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Total citations:
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Citations from 2024:
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Valishina E. A. et al. Palladium-ADC complexes as efficient catalysts in copper-free and room temperature Sonogashira coupling // Journal of Molecular Catalysis A Chemical. 2014. Vol. 395. pp. 162-171.
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Valishina E. A., Salgueiro da Silva M. A., Kinzhalov M. A., Timofeeva S. A., Buslaeva T. M., Haukka M., Pombeiro A. J. L., Boyarskiy V. P., Kukushkin V. Y., Luzyanin K. Palladium-ADC complexes as efficient catalysts in copper-free and room temperature Sonogashira coupling // Journal of Molecular Catalysis A Chemical. 2014. Vol. 395. pp. 162-171.
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TY - JOUR
DO - 10.1016/j.molcata.2014.08.018
UR - https://doi.org/10.1016/j.molcata.2014.08.018
TI - Palladium-ADC complexes as efficient catalysts in copper-free and room temperature Sonogashira coupling
T2 - Journal of Molecular Catalysis A Chemical
AU - Valishina, Elena A
AU - Salgueiro da Silva, M. A.
AU - Kinzhalov, M. A.
AU - Timofeeva, Svetlana A
AU - Buslaeva, Tatyana M
AU - Haukka, Matti
AU - Pombeiro, Armando J. L.
AU - Boyarskiy, Vadim P
AU - Kukushkin, Vadim Yu.
AU - Luzyanin, Konstantin
PY - 2014
DA - 2014/12/01
PB - Elsevier
SP - 162-171
VL - 395
SN - 1381-1169
ER -
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BibTex (up to 50 authors)
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@article{2014_Valishina,
author = {Elena A Valishina and M. A. Salgueiro da Silva and M. A. Kinzhalov and Svetlana A Timofeeva and Tatyana M Buslaeva and Matti Haukka and Armando J. L. Pombeiro and Vadim P Boyarskiy and Vadim Yu. Kukushkin and Konstantin Luzyanin},
title = {Palladium-ADC complexes as efficient catalysts in copper-free and room temperature Sonogashira coupling},
journal = {Journal of Molecular Catalysis A Chemical},
year = {2014},
volume = {395},
publisher = {Elsevier},
month = {dec},
url = {https://doi.org/10.1016/j.molcata.2014.08.018},
pages = {162--171},
doi = {10.1016/j.molcata.2014.08.018}
}