Organometallics, volume 40, issue 21, pages 3645-3658
Formation of Allylpalladium Complexes and Asymmetric Allylation Involving Modular Bridging Diamidophosphite-Sulfides Based on 1,4-Thioether Alcohols
Chuchelkin I V
1
,
Firsin I D
1
,
Perepukhov Alexander M.
2
,
Maximychev Alexander V
2
,
Dejoie Catherine
5
,
Chernyshev V. V.
3, 4
,
Zimarev Vladislav S
1, 3
,
Goulioukina N S
1, 3, 4
Publication type: Journal Article
Publication date: 2021-10-26
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 large family of P,S-bidentate diamidophosphite ligands were readily synthesized from accessible hydroxyl-thioether compounds. One type of Pd(II) cationic allylic complex with these diamidophosphites fulfilling a P-monodentate function, and three types, where the ligands act as P,S-bridging ligands (coordination polymer and head-to-head and head-to-tail dimers), were obtained. In addition, neutral Pd(II) halide complexes were generated in situ as common intermediates for both groups of cationic dimers. The structures of the ligands and complexes were elucidated by means of 2D-NMR and were confirmed by powder X-ray diffraction, as well as by DFT calculations. Asymmetric inducers of this type exhibited up to 94% ee in the Pd-mediated allylic substitution of (E)-1,3-diphenylallyl acetate with various C- and N-nucleophiles. Ee values of up to 80% were obtained in the Pd-catalyzed allylic alkylation of cinnamyl acetate with β-ketoesters. In addition, up to 61% ee was achieved in the asymmetric amination of 2-(diethoxyphosphoryl)-1-phenylallyl acetate with aniline. The effects of the diamidophosphite and thioether moieties on the catalytic activity and enantioselectivity were investigated.
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Chuchelkin I. V. et al. Formation of Allylpalladium Complexes and Asymmetric Allylation Involving Modular Bridging Diamidophosphite-Sulfides Based on 1,4-Thioether Alcohols // Organometallics. 2021. Vol. 40. No. 21. pp. 3645-3658.
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Chuchelkin I. V., Gavrilov K. N., Gavrilov V. K., Zheglov S. V., Firsin I. D., Perepukhov A. M., Maximychev A. V., Borisova N. E., Zamilatskov I. A., Tyurin V. S., Dejoie C., Chernyshev V. V., Zimarev V. S., Goulioukina N. S. Formation of Allylpalladium Complexes and Asymmetric Allylation Involving Modular Bridging Diamidophosphite-Sulfides Based on 1,4-Thioether Alcohols // Organometallics. 2021. Vol. 40. No. 21. pp. 3645-3658.
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TY - JOUR
DO - 10.1021/acs.organomet.1c00491
UR - https://doi.org/10.1021%2Facs.organomet.1c00491
TI - Formation of Allylpalladium Complexes and Asymmetric Allylation Involving Modular Bridging Diamidophosphite-Sulfides Based on 1,4-Thioether Alcohols
T2 - Organometallics
AU - Maximychev, Alexander V
AU - Zimarev, Vladislav S
AU - Perepukhov, Alexander M.
AU - Chuchelkin, I V
AU - Gavrilov, Konstantin N.
AU - Borisova, Nataliya E.
AU - Chernyshev, V. V.
AU - Gavrilov, Vladislav K
AU - Zheglov, Sergey V.
AU - Firsin, I D
AU - Zamilatskov, Ilya A.
AU - Tyurin, Vladimir S
AU - Dejoie, Catherine
AU - Goulioukina, N S
PY - 2021
DA - 2021/10/26 00:00:00
PB - American Chemical Society (ACS)
SP - 3645-3658
IS - 21
VL - 40
SN - 0276-7333
SN - 1520-6041
ER -
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@article{2021_Chuchelkin,
author = {Alexander V Maximychev and Vladislav S Zimarev and Alexander M. Perepukhov and I V Chuchelkin and Konstantin N. Gavrilov and Nataliya E. Borisova and V. V. Chernyshev and Vladislav K Gavrilov and Sergey V. Zheglov and I D Firsin and Ilya A. Zamilatskov and Vladimir S Tyurin and Catherine Dejoie and N S Goulioukina},
title = {Formation of Allylpalladium Complexes and Asymmetric Allylation Involving Modular Bridging Diamidophosphite-Sulfides Based on 1,4-Thioether Alcohols},
journal = {Organometallics},
year = {2021},
volume = {40},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021%2Facs.organomet.1c00491},
number = {21},
pages = {3645--3658},
doi = {10.1021/acs.organomet.1c00491}
}
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Chuchelkin, I. V., et al. “Formation of Allylpalladium Complexes and Asymmetric Allylation Involving Modular Bridging Diamidophosphite-Sulfides Based on 1,4-Thioether Alcohols.” Organometallics, vol. 40, no. 21, Oct. 2021, pp. 3645-3658. https://doi.org/10.1021%2Facs.organomet.1c00491.