First Tetradentate Diamidophosphite Based on [5,10,15,20-Tetrakis(4-hydroxyphenyl)porphyrinato]zinc: Synthesis, Spectral Features, Coordination, and Application in Asymmetric Pd-Catalyzed Reactions

Igor S. Mikhel,^a Konstantin N. Gavrilov,^b@ Sergey V. Zheglov,^b Ivan M. Novikov,^b Kirill P. Birin,^a Andrey Yu. Chernyadyev,^a and Vladimir S. Tyurin^a

^aA.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 119071 Moscow, Russia

^bS.A. Esenin Ryazan State University, 390000 Ryazan, Russia

^@Corresponding author E-mail: k.gavrilov@365.rsu.edu.ru

DOI: 10.6060/mhc200918g

Macroheterocycles 2021 14(1) 70-78

The synthesis of the tetradentate diamidophosphite (L) containing four 1,3,2-diazaphospholidine rings and a porphyrin moiety, its characterization and application in asymmetric Pd-catalyzed reactions are reported. The best results (up to 63 % ee) were obtained for the Pd-catalyzed allylic alkylation of (E)-1,3-diphenylallyl acetate with dimethylmalonate. The complex L[Ru(p-cymene)Cl₂]₄ was synthesized in situ and characterized by spectroscopic data. The structure of the compounds obtained is discussed based on ¹H, ¹³C, ¹³C DEPT, ³¹P, ¹H-¹³C HSQC, ¹H-¹³C HMBC, ¹H-¹H COSY, ¹H-¹H ROESY NMR spectroscopy, as well as UV-Vis and fluorescence spectroscopy.

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First Tetradentate Diamidophosphite Based on [5,10,15,20-Tetrakis(4-hydroxyphenyl)porphyrinato]zinc: Synthesis, Spectral Features, Coordination, and Application in Asymmetric Pd-Catalyzed Reactions

References: