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.
Citation:
K. N. Gavrilov, I. V. Chuchelkin, S. V. Zheglov, I. D. Firsin, V. M. Trunina, V. K. Gavrilov, N. E. Borisova, V. S. Zimarev, A. A. Denesh, N. S. Goulioukina, “Novel BIPHEN H2 based P,S-bidentate phosphoramidite ligand in palladium-catalyzed asymmetric allylation”, Mendeleev Commun., 31:5 (2021), 651–653
Linking options:
https://www.mathnet.ru/eng/mendc1011
https://www.mathnet.ru/eng/mendc/v31/i5/p651
This publication is cited in the following 4 articles:
Mariette M. Pereira, Rui M. B. Carrilho, Mário J. F. Calvete, Organophosphorus Chemistry, 2024, 1
Stéphane Bellemin-Laponnaz, Thierry Achard, “Recent Progress in Developing Thioether-Containing Ligands for Catalysis Applications”, Synthesis, 56:09 (2024), 1369
V. S. Zimarev, I. V. Chuchelkin, K. N. Gavrilov, I. A. Zamilatskov, V. A. Tafeenko, B. V. Lokshin, N. S. Goulioukina, “Neutral dinuclear palladium(II) complex containing chiral P,S-bridging diamidophosphite-thioether ligands”, Mendeleev Commun., 34:2 (2024), 195–197
K. N. Gavrilov, I. V. Chuchelkin, V. M. Trunina, I. D. Firsin, Y. P. Bityak, D. A. Fedorov, V. S. Zimarev, N. S. Goulioukina, “P,S-Bidentate Phosphoramidites with (Ra)-BINOL Core in Palladium-Catalyzed Asymmetric Allylic Substitution”, Russ J Gen Chem, 92:12 (2022), 2612
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