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Novel BIPHEN H2 based P,S-bidentate phosphoramidite ligand in palladium-catalyzed asymmetric allylation

Konstantin Nikolaevich Gavrilov 1
Konstantin Nikolaevich Gavrilov
, 
Ilya Valer'evich Chuchelkin 1
Ilya Valer'evich Chuchelkin
, 
Sergey Viktorovich Zheglov 1
Sergey Viktorovich Zheglov
, 
Ilya Dmitrievich Firsin 1
Ilya Dmitrievich Firsin
, 
Valeria Mikhailovna Trunina 1
Valeria Mikhailovna Trunina
, 
Vladislav Konstantinovich Gavrilov 1
Vladislav Konstantinovich Gavrilov
, 
Natalia Evgen'evna Borisova 2
Natalia Evgen'evna Borisova
, 
Vladislav Sergeyevich Zimarev 1, 2
Vladislav Sergeyevich Zimarev
, 
Andrey Andreevich Denesh 2
Andrey Andreevich Denesh
, 
Nataliya Sergeevna Goulioukina 1, 2, 3
Nataliya Sergeevna Goulioukina
10.1016/j.mencom.2021.09.019
Published 2021-09-08
Communication , Volume 31, Issue 5, 651-653
4
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Gavrilov K. N. et al. Novel BIPHEN H2 based P,S-bidentate phosphoramidite ligand in palladium-catalyzed asymmetric allylation // Mendeleev Communications. 2021. Vol. 31. No. 5. pp. 651-653.
GOST all authors (up to 50) Copy
Gavrilov K. N., Chuchelkin I. V., Zheglov S. V., Firsin I. D., Trunina V. M., Gavrilov V. K., Borisova N. E., Zimarev V. S., Denesh A. A., Goulioukina N. S. Novel BIPHEN H2 based P,S-bidentate phosphoramidite ligand in palladium-catalyzed asymmetric allylation // Mendeleev Communications. 2021. Vol. 31. No. 5. pp. 651-653.
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TY - JOUR
DO - 10.1016/j.mencom.2021.09.019
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.019
TI - Novel BIPHEN H2 based P,S-bidentate phosphoramidite ligand in palladium-catalyzed asymmetric allylation
T2 - Mendeleev Communications
AU - Gavrilov, Konstantin Nikolaevich
AU - Chuchelkin, Ilya Valer'evich
AU - Zheglov, Sergey Viktorovich
AU - Firsin, Ilya Dmitrievich
AU - Trunina, Valeria Mikhailovna
AU - Gavrilov, Vladislav Konstantinovich
AU - Borisova, Natalia Evgen'evna
AU - Zimarev, Vladislav Sergeyevich
AU - Denesh, Andrey Andreevich
AU - Goulioukina, Nataliya Sergeevna
PY - 2021
DA - 2021/09/08
PB - Mendeleev Communications
SP - 651-653
IS - 5
VL - 31
ER -
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@article{2021_Gavrilov,
author = {Konstantin Nikolaevich Gavrilov and Ilya Valer'evich Chuchelkin and Sergey Viktorovich Zheglov and Ilya Dmitrievich Firsin and Valeria Mikhailovna Trunina and Vladislav Konstantinovich Gavrilov and Natalia Evgen'evna Borisova and Vladislav Sergeyevich Zimarev and Andrey Andreevich Denesh and Nataliya Sergeevna Goulioukina},
title = {Novel BIPHEN H2 based P,S-bidentate phosphoramidite ligand in palladium-catalyzed asymmetric allylation},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.019},
number = {5},
pages = {651--653},
doi = {10.1016/j.mencom.2021.09.019}
}
MLA
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Gavrilov, Konstantin Nikolaevich, et al. “Novel BIPHEN H2 based P,S-bidentate phosphoramidite ligand in palladium-catalyzed asymmetric allylation.” Mendeleev Communications, vol. 31, no. 5, Sep. 2021, pp. 651-653. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.019.

Keywords

allylic substitution
asymmetric catalysis
homogeneous catalysis
P,S-ligands
Palladium complexes
phosphoramidites

Abstract

The reaction of P,S-phosphoramidite bearing (Ra)-BIPHEN H2 core and exocyclic amino sulfide as the new ligand with [Pd(ppp-allyl)Cl]2 in the presence of AgBF4 yielded a cationic metallochelate [Pd(ppp-allyl)(L)]BF4. This new chiral inducer provided up to 90% ee in the Pd-mediated allylic substitution reaction of (E)-1,3-diphenylallyl acetate with various C- and N-nucleophiles. In the Pd-catalyzed amination of 2-diethoxyphosphoryl-1-phenylallyl acetate with aniline, ee values up to 57% were achieved.

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