Organometallics, volume 42, issue 15, pages 1985-1996
Hemilabile Diamidophosphite-Thioether Ligands with a β-Hydroxy Sulfide Backbone: Palladium(II) Complexes and Asymmetric Allylic Substitution
Chuchelkin I V
1
,
Zheglov Sergey V
1
,
Firsin Ilya D
1
,
Bityak Yan P.
3
,
Maloshitskaya Olga A
2
,
Tafeenko Victor A.
2
,
Zimarev Vladislav S
1, 2
,
Goulioukina Nataliya S
1, 2, 4
Publication type: Journal Article
Publication date: 2023-07-07
Journal:
Organometallics
Quartile SCImago
Q1
Quartile WOS
Q2
Impact factor: 2.8
ISSN: 02767333, 15206041
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
A series of structurally diverse diamidophosphite-sulfides were synthesized from 1,2-thioether alcohols. With respect to Pd(II), these hemilabile ligands showed the ability to form both P,S-chelates and complexes with two ligands connected to the metal P-monodentately. The structures of the ligands and complexes were confirmed by two-dimensional (2D) NMR spectroscopy and single-crystal X-ray diffraction. These stereoselectors provided up to 98% ee in the Pd-catalyzed asymmetric allylic substitution of (E)-1,3-diphenylallyl acetate with C- and N-nucleophiles and up to 78% ee in the Pd-mediated allylic alkylation of cinnamyl acetate with β-ketoesters. Furthermore, up to 71% ee was achieved in the rare reaction between 2-(diethoxyphosphoryl)-1-phenylallyl acetate and aniline. The effects of the structural parameters, reaction conditions, and ligand-to-metal ratio on the catalytic results are discussed. Due to the ability of the ligands to form structurally different catalytic species, a pronounced dependence of the asymmetric induction on the ligand-to-metal ratio is shown.
Citations by journals
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1
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Organic and Biomolecular Chemistry
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Organic and Biomolecular Chemistry
1 publication, 50%
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Synthesis
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Synthesis
1 publication, 50%
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1
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Citations by publishers
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
1 publication, 50%
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Thieme
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Thieme
1 publication, 50%
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1
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Gavrilov K. N. et al. Hemilabile Diamidophosphite-Thioether Ligands with a β-Hydroxy Sulfide Backbone: Palladium(II) Complexes and Asymmetric Allylic Substitution // Organometallics. 2023. Vol. 42. No. 15. pp. 1985-1996.
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Gavrilov K. N., Chuchelkin I. V., Gavrilov V. K., Zheglov S. V., Firsin I. D., Trunina V. M., Borisova N. E., Bityak Y. P., Maloshitskaya O. A., Tafeenko V. A., Zimarev V. S., Goulioukina N. S. Hemilabile Diamidophosphite-Thioether Ligands with a β-Hydroxy Sulfide Backbone: Palladium(II) Complexes and Asymmetric Allylic Substitution // Organometallics. 2023. Vol. 42. No. 15. pp. 1985-1996.
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TY - JOUR
DO - 10.1021/acs.organomet.3c00212
UR - https://doi.org/10.1021%2Facs.organomet.3c00212
TI - Hemilabile Diamidophosphite-Thioether Ligands with a β-Hydroxy Sulfide Backbone: Palladium(II) Complexes and Asymmetric Allylic Substitution
T2 - Organometallics
AU - Gavrilov, Konstantin N.
AU - Chuchelkin, I V
AU - Gavrilov, Vladislav K
AU - Zheglov, Sergey V
AU - Firsin, Ilya D
AU - Trunina, Valeria M
AU - Borisova, Nataliya E.
AU - Bityak, Yan P.
AU - Maloshitskaya, Olga A
AU - Tafeenko, Victor A.
AU - Zimarev, Vladislav S
AU - Goulioukina, Nataliya S
PY - 2023
DA - 2023/07/07 00:00:00
PB - American Chemical Society (ACS)
SP - 1985-1996
IS - 15
VL - 42
SN - 0276-7333
SN - 1520-6041
ER -
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@article{2023_Gavrilov,
author = {Konstantin N. Gavrilov and I V Chuchelkin and Vladislav K Gavrilov and Sergey V Zheglov and Ilya D Firsin and Valeria M Trunina and Nataliya E. Borisova and Yan P. Bityak and Olga A Maloshitskaya and Victor A. Tafeenko and Vladislav S Zimarev and Nataliya S Goulioukina},
title = {Hemilabile Diamidophosphite-Thioether Ligands with a β-Hydroxy Sulfide Backbone: Palladium(II) Complexes and Asymmetric Allylic Substitution},
journal = {Organometallics},
year = {2023},
volume = {42},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021%2Facs.organomet.3c00212},
number = {15},
pages = {1985--1996},
doi = {10.1021/acs.organomet.3c00212}
}
Cite this
MLA
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Gavrilov, Konstantin N., et al. “Hemilabile Diamidophosphite-Thioether Ligands with a β-Hydroxy Sulfide Backbone: Palladium(II) Complexes and Asymmetric Allylic Substitution.” Organometallics, vol. 42, no. 15, Jul. 2023, pp. 1985-1996. https://doi.org/10.1021%2Facs.organomet.3c00212.