10.1002/ejoc.201800767
European Journal of Organic Chemistry
COMMUNICATION
6.61 (s, 1H), 4.78 (s, 2H), 0.94 (s, 9H), 0.14 (s, 6H). 13C NMR (101 MHz,
CDCl3) δ 177.7, 161.0, 146.9, 140.2, 130.9, 129.4, 129.2, 125.7, 110.4,
58.9, 25.9, 18.5, -5.2. IR (cm-1) ν 2928, 2856, 1768, 1668, 1538, 1449,
1357, 1255, 1089, 765. HRMS m/z calculated for C18H25O3Si [M+H]+:
317.1567; found 317.1566.
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5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(4-methoxyphenyl)furan-2-
carbaldehyde (11b): Prepared according to general procedure from (E)-
4-(((5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(4-methoxyphenyl)furan-2-
yl)methylene)amino)-N,N-dimethylaniline 10hb (23.6 mg, 0.05 mmol).
15.1 mg of product 11b was obtained as a brown oil (86% yield). 1H NMR
(400 MHz, CDCl3) δ 9.67 (s, 1H), 7.52 (d, J = 8.8 Hz, 2H), 6.99 (d, J =
8.8 Hz, 2H), 6.57 (s, 1H), 4.76 (s, 2H), 3.86 (s, 3H), 0.94 (s, 9H), 0.13 (s,
6H). 13C NMR (101 MHz, CDCl3) δ 177.7, 160.9, 160.6, 146.7, 139.9,
130.4, 130.4, 123.2, 114.6, 114.5, 110.9, 110.3, 58.9, 55.6, 25.9, 18.5, -
5.2. IR (cm-1) ν 2929, 2856, 1765, 1663, 1541, 1356, 1249, 1032, 777.
HRMS m/z calculated for C19H27O4Si [M+H]+: 347.1673; found 347.1669.
Acknowledgements
The authors would like to acknowledge Horizon 2020 ERANet-
LAC project CelluloseSynThech for financial support (ref.
ELAC2014/BEE-0341), as well as CNRS, Sorbonne Université
and Labex Michem (Investissements d'Avenir programme, ref.
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a Ciência e
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Keywords: C-H activation • ruthenium • furfurals • boronate
derivatives • imines
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