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X. Zhao et al.: The oxidative coupling between benzaldehyde derivatives
J=3Hz), 7.39 (t, 1H, H-5', J=6Hz), 7.38 (t, 1H, H-3', J=3Hz), ppm. IR (KBr): 3057, 2954, 2912, 2849, 2214, 1951, 1598, 1266
7.37 (s, 1H, H-1'), 7.36 (s, 1H, H-2'), 7.35 (t, 1H, H-4', J=3Hz). cm-1. (See Figures S28-S30 of Supporting Information)
13C-NMR (150 MHz, CDCl3, TMS, δ): 72.65, 80.54, 120.73,
3-phenyl-6,8-dibromo-1H-chromen-4-one
(3g):
127.65, 128.19, 131.72 ppm. IR (KBr): 3063, 2964, 2924, 2851, The compound was obtained in 12.7% yield as a brown
2218, 1951, 1485, 1023 cm-1. (See Figures S13-S15 of Sup- oil. H-NMR (600 MHz, CDCl3, TMS, δ): 7.54, (s, 2H, H-2,
porting Information)
1
H-5), 7.53 (d, 2H, H-7, J=1.2Hz), 7.39 (s, 1H, H=4'), 7.38 (t, 1H,
3-phenyl-1H-chromen-4-one (3b): The compound H-5', J=6Hz), 7.37 (s, 1H, H-3'), 7.36 (s, 1H, H-1'), 7.34 (s, 1H,
was obtained in 88.3% yield as a brown oil. 1H-NMR (600 H-2'), 7.33 (d, 1H, H-4', J=1.2Hz). 13C-NMR (150 MHz, CDCl3,
MHz, CDCl3, TMS, δ): 7.63 (s, 2H, H-2, H-5), 7.62 (d, 3H, H-6, TMS, δ): 72.89, 80.53, 120.86, 127.42, 128.23, 131.44 ppm. IR
H-7, H-8, J=1.2Hz), 7.52 (t, 1H, H-4', J=3Hz), 7.51 (t, 1H, H-5', (KBr): 3053, 2966, 2917, 2857, 2144, 1880, 1484, 1260 cm-1.
J=6Hz), 7.50 (t, 1H, H-3', J=3Hz), 7.47 (s, 1H, H-1'), 7.46 (s, 1H, (See Figures S31-S33 of Supporting Information)
13
H-2'), 7.45 (t, 1H, H-4', J=3Hz). C-NMR (150 MHz, CDCl3,
TMS, δ): 77.24, 81.57, 121.83, 128.46, 129.23, 132.53 ppm. IR Instruments: The molecular structures of the products
(KBr): 3050, 2953, 2926, 2855, 2191, 1741, 1485, 1252 cm-1. were determined by NMR [Bruker, Germany; 1H (600 MHz)
13
(See Figures S16-S18 of Supporting Information)
and C (150 MHz)] and IR [Perkin-Elmer, America; Spect-
3-phenyl-7,8-dihydroxy-1H-chromen-4-one (3c): rum One B IR spectrophotometer]. Yield = Actual product
The compound was obtained in 69.7% yield as a brown weight ÷Theoretical product weight. Theoretical product
1
oil. H-NMR (600 MHz, CDCl3, TMS, δ): 7.54 (d, 2H, H-2, weight = Theoretical mole number of product × molecular
H-5, J=2.4Hz), 7.53 (d, 1H, H-6, J=3.6Hz), 7.39 (t, 1H, H=4', weight of product.
J=3Hz), 7.38 (t, 1H, H-5', J=6Hz), 7.37 (t, 1H, H-3', J=3Hz),
7.35 (s, 1H, H-1'), 7.34 (d, 1H, H-2', J=1.2Hz), 7.33 (t, 1H, H-4', Acknowledgments: Financial and facility support for this
13
J=3.6Hz). C-NMR (150 MHz, CDCl3, TMS, δ): 73.91, 81.56, research came from the Fundamental Research Funds
121.82, 128.45, 129.22, 132.52 ppm. IR (KBr): 3064, 2973, in Heilongjiang provincial universities (YSTSXK201862
2918, 2198, 1961, 1487, 1460, 1013 cm-1. (See Figures S19-S21 135309110, 135309503), and the National Natural
of Supporting Information)
Science Foundation of Heilongjiang province, China
3-phenyl-5,7-dihydroxy-1H-chromen-4-one (3d): (LH2019B032).
The compound was obtained in 22.6% yield as a brown
1
oil. H-NMR (600 MHz, CDCl3, TMS, δ): 7.54, (d, 2H, H-2,
References
[1] Matsumoto K, Tachikawa S, Hashimoto N, Nakano R,
J=2.4Hz), 7.53 (d, 2H, H-6, H-8, J=3.6Hz), 7.39 (t, 1H, H=4',
J=3Hz), 7.38 (t, 1H, H-5', J=6Hz), 7.37 (t, 1H, H-3', J=3Hz),
7.36 (s, 1H, H-1'), 7.34 (d, 1H, H-2', J=1.2Hz), 7.33 (t, 1H, H-4',
J=3Hz). 13C-NMR (150 MHz, CDCl3, TMS, δ): 73.93, 81.57,
121.81, 128.46, 129.23, 132.53 ppm. IR (KBr): 2978, 2931,
2912, 2891, 1714, 1443, 1055, 882 cm-1. (See Figures S22-S24
of Supporting Information)
Yoshida M, Shindo M. Aerobic C-H oxidation of arenes using
a recyclable, heterogeneous rhodium catalyst. J Org Chem.
2017;82:4305–16.
[2] Elouarzaki K, Goff AL, Holzinger M, Thery J, Cosnier S.
Electrocatalytic oxidation of glucose by rhodium porphy-
rinfunctionalized MWCNT electrodes: application to a fully
molecular catalyst-based glucose/O2 fuel cell. J Am Chem Soc.
2012;134:14078–85.
[3] Ghorai D, Choudhury J. Rhodium(III)-N-Heterocyclic
carbene-driven cascade C-H activation catalysis. ACS Catal.
2015;5:2692–6.
[4] Luo X, Bai R, Liu S, Shan C, Chen C, Lan Y. Mechanism of
rhodium-catalyzed formyl activation: a computational study.
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[5] Abe S, Hirata K, Ueno T, Morino K, Shimizu N, Yamamoto M, et al.
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rhodium(I) catalyst for the polymerization of arylacetylenes
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3-phenyl-6-chloro-1H-chromen-4-one (3e): The
compound was obtained in 49.5% yield as a brown oil.
1H-NMR (600 MHz, CDCl3, TMS, δ): 7.55, (s, 2H, H-2, H-5),
7.54 (d, 2H, H-7, H-8, J=1.2Hz), 7.39 (s, 1H, H=4'), 7.38 (s, 1H,
H-5'), 7.37 (s, 1H, H-3'), 7.36 (s, 1H, H-1'), 7.35 (s, 1H, H-2'),
7.33 (d, 1H, H-4'). 13C-NMR (150 MHz, CDCl3, TMS, δ): 72.99,
80.54, 118.45, 120.82, 128.26, 127.49, 131.39 ppm. IR (KBr):
3047, 2949, 2921, 2848, 2142, 1951, 1660, 1468 cm-1. (See
Figures S25-S27 of Supporting Information)
3-phenyl-6-bromo-1H-chromen-4-one (3f): The
compound was obtained in 29.3% yield as a brown oil.
1H-NMR (600 MHz, CDCl3, TMS, δ): 7.54, (s, 2H, H-2, H-5),
7.53 (d, 2H, H-7, H-8, J=1.2Hz), 7.39 (s, 1H, H=4'), 7.37 (t, 1H,
H-5', J=6Hz), 7.36 (s, 1H, H-3'), 7.35 (s, 1H, H-1'), 7.34 (s, 1H,
[7] Yang H, Huo N, Yang P, Pei H, Lv H, Zhang X. Rhodium catalyzed
asymmetric hydrogenation of 2-pyridine ketones. Org Lett.
2015;17:4144–7.
13
H-2'), 7.33 (t, 1H, H-4', J=3Hz). C-NMR (150 MHz, CDCl3,
TMS, δ): 72.91, 80.47, 118.78, 120.85, 127.42, 128.18, 131.47
Unauthenticated
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