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ISSN 1998-9539

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. Tyurina

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

 

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.