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S. Vásquez-Céspedes et al.
Letter
Synlett
Supporting Information
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Supporting information for this article is available online at
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To a 10 mL Schlenk tube with a magnetic stirring bar was added
N-(o-tolyl)pivalamide (57.3 mg, 0.30 mmol), diphenyliodonium
triflate (258 mg, 0.60 mmol), and CuO/Fe3O4 (75 mg, 0.0083
mmol). Then, DCE (3.0 mL) was added under air and the reac-
tion stirred at 70 °C for 22 h. The reaction mixture was allowed
to cool to r.t., the catalyst was separated using a magnet, and the
crude reaction was concentrated in vacuo and purified by flash
column chromatography.
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Sawama, Y.; Sajiki, H. Adv. Synth. Catal. 2016, 358, 3145.
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Gilligan, R. E.; Cooke, M. L.; Phipps, R. J.; Gaunt, M. J. Angew.
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Analytical Data for 3a
1H NMR (300 MHz, CDCl3): δ = 8.21 (d, J = 1.8, 1 H), 7.65–7.57
(m, 2 H), 7.45–7.36 (m, 2 H), 7.35–7.21 (m, 4 H), 2.30 (s, 3 H),
1.37 (s, 9 H). 13C NMR (75 MHz, CDCl3): δ = 176.67, 140.79,
140.12, 136.36, 130.86, 128.77, 127.50, 127.31, 127.24, 123.49,
121.44, 39.98, 27.89, 17.47.
(27) General Procedure for ortho Arylation
To a 10 mL Schlenk tube with a magnetic stirring bar was added
N-(o-tolyl)pivalamide (57.3 mg, 0.30 mmol), diphenyliodonium
triflate (193.5 mg, 0.45 mmol), and Pd/Fe3O4 (90 mg, 0.014
mmol). Then, DCE (3.0 mL) was added under air and the reac-
tion stirred at 70 °C for 22 h. The reaction mixture was allowed
(14) (a) Daugulis, O.; Zaitsev, V. G. Angew. Chem. Int. Ed. 2005, 44,
4046. For related palladium-based ortho arylation of anilides,
see: (b) Bjorsvik, H.-R.; Elumalai, V. Eur. J. Org. Chem. 2016,
© Georg Thieme Verlag Stuttgart · New York — Synlett 2017, 28, A–F