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New Journal of Chemistry
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168.45, 148.29, 143.11, 139.43, 138.68, 133.75, 133.17, 130.08,
References
DOI: 10.1039/C9NJ02636C
129.01, 128.52, 127.13, 126.43, 126.27, 125.94, 124.85, 123.50,
116.85, 43.18, 43.03. HRMS(ESI) (Fig. S22): Calculated for
C31H28B2N3O6+ [M+H]+: 560.2159 found 560.2115.
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Synthesis of compound 15c:
The synthesis operation is the same as that of 15a. 3-Carboxy-4-
fluorobenzeneboronic acid (0.050 g, 2.75 × 10-4 mol) was instead of
3-carboxybenzeneboronic acid and yellow powder compound 15c
was obtained (0.060 g, 42%). 1H NMR (600 MHz, DMSO-d6) δ (ppm)
(Fig. S23): δ 9.41 (t, J = 5.9 Hz, 1H), 8.88 (dd, J = 5.9, 4.6 Hz, 1H),
8.36 (s, 2H), 8.30 (d, J = 8.2 Hz, 2H), 8.24 – 8.13 (m, 5H), 8.00 (d, J =
8.2 Hz, 2H), 7.88 – 7.80 (m, 1H), 7.63 (ddd, J = 18.3, 13.3, 5.4 Hz,
4H), 7.40 (dd, J = 34.1, 8.1 Hz, 4H), 4.61 (d, J = 5.8 Hz, 2H), 4.48 (d, J
= 5.9 Hz, 2H). 13C NMR (151 MHz, MeOD) δ (ppm) (Fig. S24): δ
168.46, 165.58, 160.29, 158.64, 148.29, 143.11, 139.10, 138.69,
130.08, 129.10, 129.01, 128.54, 127.12, 126.42, 126.32, 126.23,
126.21, 124.89, 123.52, 116.88, 43.18, 43.05. HRMS(ESI) (Fig. S25):
Calculated for C31H27B2FN3O6+ [M+H]+: 578.2065 found 578.2015.
Synthesis of compound 15d:
The synthesis operation is the same as that of 15a. 4-Carboxy-3-
fluorobenzeneboronic acid (0.050 g, 2.75 × 10-4 mol) was instead of
3-carboxybenzeneboronic acid and yellow powder compound 15d
was obtained (0.62 g, 43%). 1H NMR (600 MHz, MeOD) δ (ppm)
(Fig. S26): δ 8.08 (d, J = 66.6 Hz, 6H), 7.92 (s, 1H), 7.77 (s, 3H), 7.53
(d, J = 27.9 Hz, 2H), 7.35 (d, J = 21.7 Hz, 3H), 7.06 (s, 1H), 4.69 (s,
2H), 4.62 (s, 2H). 13C NMR (151 MHz, MeOD) δ (ppm) (Fig. S27): δ
168.53, 148.31, 143.17, 139.15, 138.70, 130.09, 128.98, 128.55,
127.11, 126.38, 126.32, 126.25, 124.89, 123.52, 116.91, 114.93,
114.79, 43.20, 43.05. HRMS(ESI) (Fig. S28): Calculated for
C31H27B2FN3O6+ [M+H]+: 578.2065 found 578.2018.
3.
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Synthesis of compound 15e:
The synthesis operation is the same as that of 15a. 3-Carboxy-5-
fluorobenzeneboronic acid (0.050 g, 2.75 × 10-4 mol) was instead of
3-carboxybenzeneboronic acid and yellow powder compound 15e
1
was obtained (0.070 g, 49%). H NMR (600 MHz, MeOD) δ (ppm)
(Fig. S29): 8.20 – 8.10 (m, 4H), 8.04 (s, 1H), 7.82 (dd, J = 52.3, 44.8
Hz, 4H), 7.60 – 7.44 (m, 4H), 7.40 – 7.30 (m, 3H), 4.70 (s, 2H), 4.62
(s, 2H). 13C NMR (151 MHz, MeOD) δ (ppm) (Fig. S30): 168.50,
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127.11, 126.41, 126.35, 126.32, 126.30, 124.84, 123.51, 123.49, 23.
+
116.83, 43.18. HRMS(ESI) (Fig. S31): Calculated for C31H27B2FN3O6
[M+H]+: 578.2065, found 578.2060.
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Conflicts of interest
The authors conform that this article content has no conflict of
interest.
Acknowledgements
The authors would like to thank the Innovation Project of Shandong
Academy of Medical Sciences for financial support. This work was
supported by National Natural Science Foundation of China (Grant
No. 21801158), Shandong Academy of Medical Sciences Foundation
(Grant No. 2018-17), Graduate Instructor Guidance Ability
Improvement Project of Jinan University (Grant No. JDYY1804).
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