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A. Singh, A. K. Narula
Letter
Synlett
species and on the mechanism of the reaction is in progress
in our research laboratory.
L. L.; Chen, A. J. Org. Chem. 2012, 77, 8007. (e) Goh, K. S.; Tan, C.-
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Funding Information
(13) Nakagawa, K.; Onoue, H.; Minami, K. Chem. Commun. 1966, 1, 17.
(14) Ekoue-Kovi, K.; Wolf, C. Chem. Eur. J. 2008, 14, 6302.
(15) Yoo, W.; Li, C. J. Am. Chem. Soc. 2006, 128, 13064.
The authors acknowledge the financial support provided by the Guru
Gobind Singh Indraprastha University.
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An oven-dried Schlenk tube was charged with a solution of NHC
precursor 1a (10 mol%) and CuI (10 mol%) in CH3CN (3 mL)
under N2. NaH (10 mol%) was added, and the resulting mixture
was stirred vigorously for about 20–30 min and then the appro-
priate aldehyde (2.5mmol) and amine (2.5mmol) were added to
the flask together with TBHP (3 equiv). The mixture was
refluxed for 6 h in an oil bath then cooled to r.t., filtered through
a Celite pad, and washed with H2O. The organic portion was
extracted with EtOAc, dried (Na2SO4), and purified by column
chromatography (silica gel, EtOAc–hexane).
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2,6-Difluoro-N-[2-(2-thienyl)ethyl]benzamide (4x)
White solid; yield: 521 mg (78%); mp 152–153 °C. 1H NMR (400
MHz, CDCl3): = 7.36–7.28 (m, 1 H), 7.15 (dt, J = 5.1, 1.2 Hz, 1
H), 6.96–6.83 (m, 4 H), 6.19 (br s, 1 H), 3.71 (q, J = 6.3 Hz, 2 H),
3.14 (t, J = 6.7 Hz, 2 H). 13C NMR (101 MHz, CDCl3): = 161.32,
160.55, 141.04, 131.65, 127.22, 125.75, 124.20, 114.36, 111.95,
41.51, 29.85. LC-MS: m/z [M + H]+ calcd for C13H12F2NOS:
268.0512; found: 268.0509.
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