Page 13 of 19
The Journal of Organic Chemistry
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2-(4-bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3q).8b Rf=0.5 (petroleum ether/ethyl
acetate=2/1). Eluent: petroleum ether/ethyl acetate=30/1. Yield: 40% (49 mg). White solid. Mp:
209-211 °C. 1H NMR (400 MHz, CDCl3) δ 8.58 (s, 1H), 8.21 (d, J = 7.8 Hz, 1H), 8.05 (d, J = 7.3
Hz, 1H), 7.49 (t, J = 7.6 Hz, 1H), 1.37 (s, 12H). 13C{1H} NMR (101 MHz, CDCl3) δ 172.1, 140.0,
136.6, 132.9, 128.8, 127.9, 84.2, 24.9.
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2-(4-bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3r).7a Rf=0.7 (petroleum ether/ethyl
acetate=5/1). Eluent: petroleum ether/ethyl acetate=120/1. Yield: 56% (70 mg). Yellow solid. Mp:
40-41 °C. 1H NMR (400 MHz, CDCl3) δ 8.65 (d, J = 1.3 Hz, 1H), 8.30 (dd, J = 8.2, 1.2 Hz, 1H),
8.10 (d, J = 7.3 Hz, 1H), 7.54 (t, J = 7.8 Hz, 1H), 1.37 (s, 12H). 13C{1H} NMR (101 MHz, CDCl3)
δ 147.9, 140.7, 129.4, 128.8, 125.9, 84.6, 24.9.
2-(3-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3s).7a Rf=0.8 (petroleum ether/ethyl
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acetate=20/1). Eluent: petroleum ether/ethyl acetate=200/1. Yield: 40% (48 mg). Yellow oil. H
NMR (400 MHz, CDCl3) δ 8.65 (d, J = 1.3 Hz, 1H), 8.30 (dd, J = 8.2, 1.2 Hz, 1H), 8.10 (d, J = 7.3
Hz, 1H), 7.54 (t, J = 7.8 Hz, 1H), 1.37 (s, 12H). 13C{1H} NMR (101 MHz, CDCl3) δ 134.6, 134.1,
132.7, 131.3, 129.2, 84.2, 24.9.
4,4,5,5-tetramethyl-2-(o-tolyl)-1,3,2-dioxaborolane (3t).8b Rf=0.7 (petroleum ether/ethyl
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acetate=20/1). Eluent: petroleum ether/ethyl acetate=200/1. Yield: 27% (3o mg). Yellow oil. H
NMR (400 MHz, CDCl3) δ 7.77 (d, J = 7.0 Hz, 1H), 7.40 – 7.29 (m, 1H), 7.20 – 7.14 (m, 2H), 2.55
(s, 3H), 1.36 (s, 12H). 13C{1H} NMR (101 MHz, CDCl3) δ 144.9, 135.9, 130.8, 129.8, 124.7, 83.4,
24.9, 22.3.
4,4,5,5-tetramethyl-2-(o-tolyl)-1,3,2-dioxaborolane (3u).11 Rf=0.7 (petroleum ether/ethyl
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acetate=20/1). Eluent: petroleum ether/ethyl acetate=200/1. Yield: 27% (30 mg). Yellow oil. H
NMR (400 MHz, CDCl3) δ 7.68 (d, J = 7.1 Hz, 1H), 7.38 – 7.30 (m, 2H), 7.25 – 7.20 (m, 1H), 1.37
(s, 12H). 13C{1H} NMR (101 MHz, CDCl3) δ 139.6, 136.4, 131.9, 129.4, 125.8, 84.2, 24.8.
Potassium (4-methoxyphenyl)trifluoroborate (6a).8b Yield: 37% (80 mg). White solid. Mp: 240-
242 °C. 1H NMR (400 MHz, DMSO-d6) δ 7.21 (d, J = 8.1 Hz, 2H), 6.65 (d, J = 8.0 Hz, 2H), 3.66
(s, 3H). 13C{1H} NMR (101 MHz, DMSO-d6) δ 157.6, 132.7, 112.3, 55.0.
Potassium (4-biphenyl)trifluoroborate (6b).17 Yield: 31% (80 mg). White solid. Mp: > 250 °C. 1H
NMR (400 MHz, DMSO-d6) δ 7.60 (d, J = 7.4 Hz, 2H), 7.48 – 7.35 (m, 6H), 7.29 (t, J = 7.3 Hz,
1H). 13C{1H} NMR (101 MHz, DMSO-d6) δ 141.9, 137.3, 132.4, 129.2, 127.0, 126.8, 125.1.
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