Amphiphilic PdII -NHC Complexes on 1,3-Alternate p-tert -Butylthiacalix[4]arene Platform: Synthesis and Catalytic Activities in Coupling and Hydrogenation Reactions
Vladimir Burilov
1, 2
,
Mr Bulat Kh Gafiatullin
1, 2
,
Diana Mironova
1, 2
,
Elza Sultanova
1, 2
,
Vladimir G Evtyugin
1, 2
,
Yuri N. Osin
1, 2
,
Daut R. Islamov
3, 4
,
К. Усачев
1, 2
,
S. E. Solovieva
3, 4
,
I. S. Antipin
1, 2
Publication type: Journal Article
Publication date: 2020-02-28
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
Herein we report the first example of amphiphilic PdII–NHC complexes on the thiacalix[4]arene backbone in 1,3‐alternate configuration. Relative catalytic activity of synthesized PdII–NHC complexes in Suzuki–Miyaura coupling of haloarenes with phenylboronic acid was studied. A combination of micellar and metallocomplex catalysis was observed in Suzuki–Miyaura coupling upon going from pure DMF to water/DMF 3:1: the 2‐fold increase of conversion of 4‐bromoanisole unlike pure DMF was found. Interesting feature was found using chloroarene in DMF/water: the reaction selectivity changed from heterocoupling to homo coupling of phenylboronic acid. PdII–NHC complexes demonstrated a high activity in model hydrogenation reaction of p‐nitrophenol using sodium borohydride. The most lipophilic PdII–NHC complex was found to be most active, which can be attributed with additional p‐nitrophenol preconcentration in the aggregates due to larger hydrophobic capacity of macrocycle.
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Burilov V. et al. Amphiphilic PdII -NHC Complexes on 1,3-Alternate p-tert -Butylthiacalix[4]arene Platform: Synthesis and Catalytic Activities in Coupling and Hydrogenation Reactions // European Journal of Organic Chemistry. 2020. Vol. 2020. No. 15. pp. 2180-2189.
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Burilov V., Gafiatullin M. B. Kh., Mironova D., Sultanova E., Evtyugin V. G., Osin Y. N., R. Islamov D., Усачев К., Solovieva S. E., Antipin I. S. Amphiphilic PdII -NHC Complexes on 1,3-Alternate p-tert -Butylthiacalix[4]arene Platform: Synthesis and Catalytic Activities in Coupling and Hydrogenation Reactions // European Journal of Organic Chemistry. 2020. Vol. 2020. No. 15. pp. 2180-2189.
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TY - JOUR
DO - 10.1002/ejoc.202000059
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202000059
TI - Amphiphilic PdII -NHC Complexes on 1,3-Alternate p-tert -Butylthiacalix[4]arene Platform: Synthesis and Catalytic Activities in Coupling and Hydrogenation Reactions
T2 - European Journal of Organic Chemistry
AU - Burilov, Vladimir
AU - Gafiatullin, Mr Bulat Kh
AU - Mironova, Diana
AU - Sultanova, Elza
AU - Evtyugin, Vladimir G
AU - Osin, Yuri N.
AU - R. Islamov, Daut
AU - Усачев, К.
AU - Solovieva, S. E.
AU - Antipin, I. S.
PY - 2020
DA - 2020/02/28
PB - Wiley
SP - 2180-2189
IS - 15
VL - 2020
SN - 1434-193X
SN - 1099-0690
ER -
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BibTex (up to 50 authors)
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@article{2020_Burilov,
author = {Vladimir Burilov and Mr Bulat Kh Gafiatullin and Diana Mironova and Elza Sultanova and Vladimir G Evtyugin and Yuri N. Osin and Daut R. Islamov and К. Усачев and S. E. Solovieva and I. S. Antipin},
title = {Amphiphilic PdII -NHC Complexes on 1,3-Alternate p-tert -Butylthiacalix[4]arene Platform: Synthesis and Catalytic Activities in Coupling and Hydrogenation Reactions},
journal = {European Journal of Organic Chemistry},
year = {2020},
volume = {2020},
publisher = {Wiley},
month = {feb},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202000059},
number = {15},
pages = {2180--2189},
doi = {10.1002/ejoc.202000059}
}
Cite this
MLA
Copy
Burilov, Vladimir, et al. “Amphiphilic PdII -NHC Complexes on 1,3-Alternate p-tert -Butylthiacalix[4]arene Platform: Synthesis and Catalytic Activities in Coupling and Hydrogenation Reactions.” European Journal of Organic Chemistry, vol. 2020, no. 15, Feb. 2020, pp. 2180-2189. https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202000059.