· supplementary information synthesis of coenzyme q0 through divanadium-catalyzed oxidation of...

Supplementary InformationSynthesis of coenzyme Q0 through divanadium-catalyzed oxidation of 3,4,5-

trimethoxytoluene with hydrogen peroxide

Olga V. Zalomaeva,a Vasilii Yu. Evtushok,ab Gennadii M. Maksimov,a Raisa I. Maksimovskayaa and Oxana A. Kholdeeva*ab

a Boreskov Institute of Catalysis, Pr. Ac. Lavrentieva 5, Novosibirsk 630090, Russia. E-mail: khold@catalysis.ru; Fax: +7-383-330-9573; Tel: +7-383-326-9433.b Novosibirsk State University, Pirogova str. 2, Novosibirsk 630090, Russia.

Table of contents

Figure S1. FTIR spectra of (Bu4N)3.5H1.5[γ-PW10V2O40]: initial and after catalytic reaction.

Figure S2. 51V NMR (400 MHz; 25 °C) spectrum of (Bu4N)3.3H1.7[γ-PW10V2O40] in dry CH3CN.

Figure S3. Potentiometric titration of (Bu4N)3.5H1.5[γ-PW10V2O40] with TBAOH.

Figure S4. 1H NMR (400 MHz; 25 °C) spectrum of isolated 2,3-dimethoxy-5-methyl-1,4-benzoquinone in CDCl3.

Figures S5-S9. 1H NMR spectra of other quinone products.

Electronic Supplementary Material (ESI) for Dalton Transactions.This journal is © The Royal Society of Chemistry 2017

1200 1000 800 600 400

after reaction

Wavenumber, cm-1

489

1039

1062

1150

704

1094

806

533

752

875

953

974

initial

Figure S1. FTIR spectra of (Bu4N)3.5H1.5[γ-PW10V2O40]: initial and after catalytic reaction.

- 579

- 581

- 5 80 - 5 85 - 5 75 ppm

Figure S2. 51V NMR (400 MHz; 0.0015 M, 25 °C) spectrum of (Bu4N)3.3H1.7[γ-PW10V2O40] in dry CH3CN.

0.0 0.2 0.4 0.6 0.8 1.0 1.2 1.4 1.6 1.8 2.0-600-500-400-300-200-100

0100200300400500

Pote

ntia

l, m

V

TBAOH, equiv

Figure S3. Potentiometric titration of (Bu4N)3.5H1.5[γ-PW10V2O40] with TBAOH.

Figure S4. 1H NMR (400 MHz; 25 °C) spectrum of isolated 2,3-dimethoxy-5-methyl-1,4-benzoquinone in CDCl3.

Figure S5. 1H NMR (400 MHz; 25 °C) spectrum of 2-methoxy-5-methyl-1,4-benzoquinone in reaction mixture (CD3CN) after complete conversion of substrate.

Figure S6. 1H NMR (400 MHz; 25 °C) spectrum of 2-methoxy-6-methyl-1,4-benzoquinone in reaction mixture (CD3CN) after complete conversion of substrate.

Figure S7. 1H NMR (400 MHz; 25 °C) spectrum of isolated 2,6-dimethoxy-3-methyl-1,4-benzoquinone in CDCl3.

Figure S8. 1H NMR (400 MHz; 25 °C) spectrum of 2,3-dimethoxy-1,4-benzoquinone in reaction mixture (CH3CN) after complete conversion of substrate.

Figure S9. 1H NMR (400 MHz; 25 °C) spectrum of isolated 2,6-dimethoxy-1,4-benzoquinone in CDCl3