2388
J. Maddaluno, M. Durandetti
Cluster
Synlett
Supporting Information
(f) Mesganaw, T.; Garg, N. K. Org. Process Res. 2013, 17, 29.
(g) Jerozek, R. L.; Zhang, N.; Leowanawat, P.; Bunner, M. H.;
Gutsche, N.; Pesti, A. K. R.; Olsen, J. T.; Percec, V. Org. Lett. 2014,
16, 6326. (h) Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang,
N.; Resmerita, A.-M.; Garg, N. K.; Percec, V. Chem. Rev. 2011,
111, 1346.
Supporting information for this article is available online at
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(17) Representative Procedure for the Nickel-Catalyzed Forma-
tion of Biaryls
To a solution of aryl tosylate (2 mmol, 1 equiv) in anhydrous
DMF (5 mL) under an argon atmosphere at room temperature
(or 60 °C for o-substituted or electron-donating substituents)
was added manganese (4 mmol, 2 equiv) followed by NiBr2bipy
(0.2 mmol, 0.1 equiv), then rapidly TFA (10 μL). The medium
was vigorously stirred, and the disappearance of starting mate-
rial was monitored by gas chromatography. The reaction was
stopped after the aryl tosylate was consumed (ca. 1 h). The
mixture was hydrolyzed with HCl 1 M (5 mL) and diluted with
Et2O (15 mL). The aqueous layer was extracted with Et2O (2 × 15
mL), then combined organic layers were washed with water
(2 × 15 mL) and brine (15 mL), dried over anhydrous MgSO4, and
concentrated. The crude was purified by recrystallization.
1,1′-Biphenyl18 (CAS registry number: 92-52-4)
The pure product is isolated in 91% as white crystals; mp 68 °C.
1H NMR (300 MHz, CDCl3): δ = 7.35 (t, J = 7.4 Hz, 2 H), 7.4 (t,
J = 7.7 Hz, 4 H), 7.59 (d, J = 7.8 Hz, 4 H) ppm. 13C NMR (75 MHz,
CDCl3): δ = 127.3 (2 C), 127.4, 128.9 (2 C), 141.4 ppm. MS (EI, 70
eV): m/z = 154 [M+], 77 [M/2, base].
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© Georg Thieme Verlag Stuttgart · New York — Synlett 2015, 26, 2385–2388