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P*,S-Bidentate diamidophosphite based on 3-(phenylthiomethyl)phenol

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Abstract

A new P*,S-bidentate diamidophosphite ligand 1, containing a stereogenic phosphorus atom as a part of the 1,3,2-diazaphospholidine ring, was synthesized based on 3-(phenylthiomethyl)phenol. Palladium catalysts on its basis demonstrated a high enantioselectivity in the allylic alkylation of (E)-1,3-diphenylallyl acetate with dimethyl malonate (76% ee), the amination with pyrrolidine (74% ee), and the alkylation of cinnamyl acetate with ethyl 2-oxocyclohexanecarboxylate (83% ee). The reaction of ligand 1 with [Pd(allyl)Cl]2 in the presence of AgBF4 afforded a mixture of cationic palladium complexes: chelate [Pd(allyl)1]BF4 and head-to-head binuclear complex [Pd(allyl)1]2(BF4)2.

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Authors and Affiliations

  1. S. A. Esenin Ryazan State University, 46 ul. Svobody, 390000, Ryazan, Russian Federation

    K. N. Gavrilov, I. V. Chuchelkin, V. K. Gavrilov, V. M. Trunina, I. D. Firsin, S. V. Zheglov, V. S. Zimarev & N. S. Goulioukina

  2. Moscow Institute of Physics and Technology, 9 Institutskii per., 141701, Dolgoprudny, Moscow region, Russian Federation

    Ya. P. Bityak & D. A. Fedorov

  3. Department of Chemistry, M. V. Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    V. S. Zimarev & N. S. Goulioukina

  4. A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 31 Leninsky prosp., 119071, Moscow, Russian Federation

    N. S. Goulioukina

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  1. K. N. Gavrilov
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  2. I. V. Chuchelkin
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  3. V. K. Gavrilov
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  6. S. V. Zheglov
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  9. V. S. Zimarev
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Correspondence to K. N. Gavrilov.

Additional information

This work was financially supported by the Russian Science Foundation (project No. 19-13-00197).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 5, pp. 1251–1258, May, 2023.

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Gavrilov, K.N., Chuchelkin, I.V., Gavrilov, V.K. et al. P*,S-Bidentate diamidophosphite based on 3-(phenylthiomethyl)phenol. Russ Chem Bull 72, 1251–1258 (2023). https://doi.org/10.1007/s11172-023-3897-8

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