7
B-(3-Trifluoromethylphenylboronic acid [1423-26-3] 6v38
148 mg of B-(3-Trifluoromethylphenyl)boronic acid was
obtained as a white solid starting from 225mg of 3-
(t, J = 7.3 Hz, 3H). 11B NMR (96 MHz, acetone-d6) δ (ppm) 4,1
(q, J = 53 Hz)
ACCEPTED MANUSCRIPT
Potassium
(3,4-dimethylphenyl)trifluoroborate
9f42
trifluoromethylbromobenzene following procedures B and D
Prepared from 3,4-dimethylbromobenzene on a 5 mmol scale
following procedures A and C (yield 91%) H NMR (300 MHz,
acetone-d6) δ (ppm) 7.27 (s, 1H), 7.22 (d, J = 7.3 Hz, 1H), 6.89
(d, J = 7.3 Hz, 1H), 2.18 (s, 3H), 2.17 (s, 3H). 11B NMR (96
MHz, acetone-d6) δ (ppm) 3.9 (q, J = 43 Hz).
1
(78%). H NMR (300 MHz, acetone-d6): δ (ppm) 8.09-8.06 (d, J
1
= 9Hz, 2H), 7.71-7.69 (d, J = 9Hz 2H), 7.57 (bs, 2H). 11B NMR
(96 MHz, acetone-d6): δ (ppm) 27.8. 13C NMR (75 MHz,
acetone-d6): δ (ppm) 162.3 (q, J = 247 Hz), 126.32, 124.2, 123.9,
114.2 (q, J = 4.0Hz), 113.9 (q, J = 3.9 Hz) 19F NMR (282 MHz,
DMSO-d6) δ -61.0
5,5-dimethyl-2-(1-methylethyl)-
1,3,2-Dioxaborinane
[61727-48-8] 10 43 1H NMR (300 MHz, CDCl3) δ (ppm) 3.55 (s,
4H), 0.91 (s, 13H); 11B NMR (96 MHz, CDCl3) δ (ppm) 30.7 (s);
13C NMR (75 MHz, CDCl3) δ (ppm) 71.9 (2C), 31.5, 21.7 (2C),
18.2 (2C).
4-Biphenylboronic acid [5122-94-1] 6x32 713 mg of 4-
Biphenylboronic acid was obtained as a white solid starting from
1.20 g of 4-bromobiphenyl following procedures B and D (78%).
1H NMR (300 MHz acetone-d6): δ (ppm) 8.03-8.00 (d, J = 9Hz,
2H), 7.71-7.66 (t, J = 7.5, 4H), 7.50-7.45 (t, J = 7.5, 2H), 7.40-
7.35 (m, 1H), 7.29 (bs, 2H). 11B NMR (96 MHz, acetone-d6): δ
(ppm) 29.1. 13C NMR (75 MHz, acetone-d6): δ (ppm) 142.6,
140.9, 134.8, 128.8, 127.5, 126.9, 126.0.
Potassium trifluoroisopropylborate [1041642-13-0] 1144 1H
NMR (300 MHz, acetone-d6) δ (ppm) 0.75 (d, 6H, J = 7.1 Hz),
0.48-0.25 (h, 1H, J = 7.1 Hz, CH) ; 11B NMR (96 MHz, acetone-
d6) δ (ppm) 5.8 (q, JB-F = 56 Hz); 13C NMR (75 MHz, acetone-d6)
δ (ppm) 18.9.
B-(2-thiophenyl)boronic acid [6165-68-0] 6y32 105 mg of 2-
thienylboronic acid was obtained as a pale yellow solid starting
from 163 mg of 4-fluoro-2-bromothiophene following procedures
1
Potassium ethyltrifluoroborate [882871-21-8] 12 H NMR
(300 MHz, DMSO-d6) δ (ppm) 0.65 (t, 3H, J = 7.8 Hz, CH3), -
0.2-0 (m, 2H, CH2); 11B NMR (96 MHz, DMSO-d6) δ (ppm) 5.03
(q, JB-F = 63 Hz); 13C NMR (75 MHz, DMSO-d6) δ (ppm) 9.8.
1
B and D (82%). H NMR (300 MHz, acetone-d6): δ (ppm) 7.69
(d, J = 4.4 Hz, 2H), 7.32 (bs, 2H), 7.17 (dd, J = 4.5 Hz, J = 3.6
Hz, 1H). 11B NMR (96 MHz, acetone-d6): δ (ppm) 26.9 13C NMR
(75 MHz, acetone-d6): δ (ppm) 137.0, 132.7, 129.3
5. Acknowledgment
We thank the CNRS and the “Ministere de l’Education
Nationale et de la Recherche”,France for financial support.
B-(2-(diphenylphosphino)phenyl)boronic acid [1187936-
76-0] 6z39 prepared from 2-bromotriphenylphosphine on a 5
mmol scale following procedures B and D (yield 70%) H NMR
1
(300 MHz, acetone-d6) δ (ppm) 8.12-8.03 (m, 4H), 7.87-7,81 (m,
3H), 7.77-7.69 (m, 4H), 7.63-7.56 (m, 1H), 7.53-7.44 (m, 1H),
7.41-7.33 (m, 1H). 11B NMR (96 MHz, acetone-d6) δ (ppm) 32.0.
31P NMR (122 MHz, acetone-d6) δ (ppm) -13.3.
References
1.
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3.
4.
5.
6.
7.
Hamilton, C. W.; Baker, R. T.; Staubitz, A.; Manners, I.
Chem. Soc. Rev. 2009, 38, 279-293.
Staubitz, A.; Robertson, A. P. M.; Manners, I. Chem. Rev.
2010, 110, 4079-4124.
Staubitz, A.; Robertson, A. P. M.; Sloan, M. E.; Manners,
I. Chem. Rev. 2010, 110, 4023-4078.
Yang, X.; Fox, T.; Berke, H. Tetrahedron 2011, 67, 7121-
7127.
Haddenham, D.; Pasumansky, L.; DeSoto, J.; Eagon, S.;
Singaram, B. J. Org. Chem. 2009, 74, 1964-1970.
Couturier, M.; Tucker, J. L.; Andresen, B. M.; Dubé, P.;
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Guerrand, H. D. S.; Marciasini, L. D.; Jousseaume, M.;
Vaultier, M.; Pucheault, M. Chem. Eur. J. 2014, 5573–
5579.
potassium trifluoro(phenyl)borate [153766-81-5] 9a40
prepared from bromobenzene on a 5 mmol scale following
1
procedures A and C (yield 95%) H NMR (300 MHz, acetone-
d6,) 7.47 (d, J = 6,6 Hz, 2H), 6.99–7.10 (m, 3H). 11B NMR (96
MHz, acetone-d6) δ (ppm) 3,0 (q, J = 54 Hz)
potassium (2-methylphenyl)trifluoroborate [274257-34-0]
9b41 prepared from 2-bromotoluene on a 5 mmol scale following
procedures A and C (yield 96%) 1H NMR (300 MHz, acetone-d6)
δ (ppm) 7.47 (d, J = 6,8 Hz, 1H), 6.96–6.86 (m, 3H), 2.90 (s,
3H). NMR 13C (75 MHz, acetone-d6) 140.9, 131.8, 128.2, 125.2,
123.2, 21.2. 11B NMR (96 MHz, acetone-d6) δ (ppm) 3.8 (q, J =
56 Hz)
8.
9.
Pucheault, M.; Guerrand, H.; Marciasini, L.; Vaultier, M.,
04/12/2013, EP 13306667.0
Pascu, O.; Marciasini, L.; Marre, S.; Vaultier, M.;
Pucheault, M.; Aymonier, C. Nanoscale 2013, 5, 12425-
12431.
Potassium (3-methylphenyl)trifluoroborate [850623-42-6]
9c42 prepared from 3-bromotoluene on a 5 mmol scale following
procedures A and C (yield 89%) 1H NMR (300 MHz, acetone-d6)
δ (ppm) 7.37–7.21 (m, 2H), 6,99 (t, J = 7.3, 1H), 6.86 (d, J = 7.4,
1H), 2,23 (s, 3H). 11B NMR (96 MHz, acetone-d6) δ (ppm) 3.8 (q,
J = 53 Hz).
10.
11.
12.
Marciasini, L.; Richy, N.; Vaultier, M.; Pucheault, M.
Chem. Commun. 2012, 48, 1553-1555.
Gendrineau, T.; Marre, S.; Vaultier, M.; Pucheault, M.;
Aymonier, C. Angew. Chem. Int. Ed. 2012, 51, 8525-8528.
Euzenat, L.; Horhant, D.; Ribourdouille, Y.; Duriez, C.;
Alcaraz, G.; Vaultier, M. Chem. Commun. 2003, 2280-
2281.
Potassium (4-methylphenyl)trifluoroborate [216434-82-1]
9d40 prepared from 4-bromotoluene on a 5 mmol scale following
procedures A and C (yield 96%) 1H NMR (300 MHz, acetone-d6)
δ (ppm) 7.36 (d, J = 7.6 Hz, 2H), 6,92 (d, J = 7.6 Hz, 2H), 2.22
(s, 3H). 11B NMR (96 MHz, acetone-d6) δ (ppm) 3.8 (q, J = 52
Hz).
13.
14.
15.
16.
Marciasini, L. D.; Vaultier, M.; Pucheault, M. Tetrahedron
Lett. 2014, 55, 1702-1705.
Marciasini, L. D.; Richy, N.; Vaultier, M.; Pucheault, M.
Adv. Synth. Catal. 2013, 355, 1083-1088.
Pucheault,
WO2014009169
Potassium (4-n-butylphenyl)trifluoroborate [1412414-09-
M.;
Marciasini,
L.;
Vaultier,
M.,
5] 9e42 prepared from 4-butylbromobenzene on a 5 mmol scale
1
following procedure A and C (yield 85%) H NMR (300 MHz,
Bailey, C. L.; Murphy, C. L.; Clary, J. W.; Eagon, S.;
acetone-d6) δ (ppm) 7,38 (d, J = 7.7 Hz, 2H), 6,93 (d, J = 7.5 Hz,
2H), 2.56–2.44 (m, 2H), 1.65–1.46 (m, 2H), 1.33 (m, 2H), 0.90
Gould, N.; Singaram, B. Heterocycles 2012, 86, 331-341.