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., 2021, Volume 31, Issue 5,Pages <nobr>651

This article is cited in 4 papers

Communications

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

K. N. Gavrilov^a, I. V. Chuchelkin^a, S. V. Zheglov^a, I. D. Firsin^a, V. M. Trunina^a, V. K. Gavrilov^a, N. E. Borisova^b, V. S. Zimarev^ab, A. A. Denesh^b, N. S. Goulioukina^abc

^a Department of Chemistry, S.A. Esenin Ryazan State University, Ryazan, Russian Federation
^b Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
^c A.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: The reaction of P,S-phosphoramidite bearing (R_a)-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.

Keywords: asymmetric catalysis, homogeneous catalysis, allylic substitution, palladium complexes, phosphoramidites, P,S-ligands.

Language: English

DOI: 10.1016/j.mencom.2021.09.019

	*Supplementary materials:*
		Supplementary_data_1.pdf	8.0 Mb