Green protocol of arylfluorenes derivatives by Suzuki reaction
J = 7.3 Hz, 2H, Ar-H), 3.93 (s, 2H, CH2). 13C NMR (101 MHz, CDCl3,
δ, ppm): 147.77 (Ar-C), 147.10 (Ar-C), 143.86 (Ar-C), 143.37 (Ar-C),
141.52 (Ar-C), 140.55 (Ar-C), 139.38 (Ar-C), 135.53 (Ar-C), 129.22
(Ar-C), 127.76 (Ar-C), 126.77 (Ar-C), 126.56 (Ar-C), 125.47 (Ar-C),
124.96 (Ar-C), 124.38 (Ar-C), 124.03 (Ar-C), 123.23 (Ar-C), 122.85
(Ar-C), 120.04 (Ar-C), 119.81 (Ar-C), 36.95 (C, CH2). MS (ESI): m/z calcd
for C21H22N [M ꢁ H]+ 408.2; found 408.2. Elemental analysis: calcd
for C31H23N (%): C, 90.92; H, 5.66; found (%): C, 90.96; H, 5.64.
2-(3,5-Dimethylphenyl)-9H-fluorene (7c)
1
Light yellow solid, m.p. 165–166 °C. H NMR (400 MHz, CDCl3, δ,
ppm): 7.85 (t, J = 7.0 Hz, 2H, Ar-H), 7.81 (s, 1H, Ar-H), 7.66 (d,
J = 7.9 Hz, 1H, Ar-H), 7.60 (d, J = 7.4 Hz, 1H, Ar-H), 7.44 (t,
J = 7.4 Hz, 1H, Ar-H), 7.37 (d, J = 7.4 Hz, 3H, Ar-H), 7.34 (s, 1H, Ar-
H), 7.06 (s, 1H, Ar-H), 3.99 (s, 2H, CH2), 2.46 (s, 6H, CH3). 13C NMR
(101 MHz, CDCl3, δ, ppm): 143.83 (Ar-C), 143.51 (Ar-C), 141.55 (Ar-
C), 140.82 (Ar-C), 140.18 (Ar-C), 138.29 (Ar-C), 128.83 (Ar-C), 126.84
(Ar-C), 126.68 (Ar-C), 126.06 (Ar-C), 125.18 (Ar-C), 125.07 (Ar-C),
123.84 (Ar-C), 120.04 (Ar-C), 119.96 (Ar-C), 37.03 (C, CH2), 21.49 (C,
CH3). MS (ESI): m/z calcd for C21H17 [M ꢁ H]+ 269.1; found 269.2. El-
emental analysis: calcd for C23H16 (%): C, 93.71; H, 6.29; found (%): C,
93.76; H, 6.24.
3-(9H-Fluoren-2-yl)-9-phenyl-9H-carbazole (7h)
1
Yellow solid, m.p. 191–192 °C. H NMR (400 MHz, CDCl3, δ, ppm):
8.50 (s, 1H, Ar-H), 8.30 (d, J = 7.6 Hz, 1H, Ar-H), 7.96 (s, 1H, Ar-H),
7.90 (dd, J = 14.6, 7.7 Hz, 2H, Ar-H), 7.84–7.74 (m, 2H, Ar-H), 7.64
(m, J = 13.4, 5H, Ar-H), 7.53 (d, J = 8.6 Hz, 4H, Ar-H), 7.47 (t,
J = 7.5 Hz, 1H, Ar-H), 7.44–7.35 (m, 2H, Ar-H), 4.03 (s, 2H, CH2). 13
C
2-(3,5-Bis (trifluoromethyl)phenyl)-9H-fluorene (7d)
NMR (101 MHz, CDCl3, δ, ppm): 144.06 (Ar-C), 143.53 (Ar-C), 141.70
(Ar-C), 141.48 (Ar-C), 140.77 (Ar-C), 140.42 (Ar-C), 140.35 (Ar-C),
137.82 (Ar-C), 133.86 (Ar-C), 129.98 (Ar-C), 127.54 (Ar-C), 127.13
(Ar-C), 126.89 (Ar-C), 126.62 (Ar-C), 126.24 (Ar-C), 126.22 (Ar-C),
125.66 (Ar-C), 125.12 (Ar-C), 124.07 (Ar-C), 123.97 (Ar-C), 123.68
(Ar-C), 120.49 (Ar-C), 120.22 (Ar-C), 120.19 (Ar-C), 119.97 (Ar-C),
118.87 (Ar-C), 110.10 (Ar-C), 110.03 (Ar-C), 37.13 (C, CH2). MS (ESI):
m/z calcd for C21H20N [M ꢁ H]+ 406.2; found 406.3. Elemental anal-
ysis: calcd for C31H21N (%): C, 91.37; H, 5.19; found (%): C, 91.42; H,
5.15.
1
Light yellow solid, m.p. 153–154 °C. H NMR (400 MHz, CDCl3, δ,
ppm): 8.10 (s, 2H), 7.95–7.80 (m, 3H), 7.79 (s, 1H, Ar-H), 7.61 (dd,
J = 11.0, 7.6 Hz, 2H, Ar-H), 7.44 (t, J = 7.6 Hz, 1H, Ar-H), 7.38 (t,
J = 7.6 Hz, 1H, Ar-H), 3.98 (s, 2H, CH2). 13C NMR (101 MHz, CDCl3,
δ, ppm): 144.36 (Ar-C), 143.61 (Ar-C), 143.58 (Ar-C), 142.56 (Ar-C),
140.81 (Ar-C), 136.58 (Ar-C), 132.32 (q, Ar-C), 127.56 (Ar-C), 127.36
(Ar-C), 127.09 (Ar-C), 127.01 (Ar-C), 126.08 (Ar-C), 125.16 (Ar-C),
124.85 (Ar-C), 123.80 (Ar-C), 122.14 (Ar-C), 120.64 (Ar-C), 120.51
(Ar-C), 120.29 (Ar-C), 119.43 (Ar-C), 36.96 (C, CH2). MS (ESI): m/z calcd
for C21H11F6 [M ꢁ H]+ 377.1; found 377.5. Elemental analysis: calcd
for C21H18 (%): C, 93.29; H, 6.71; found (%): C, 93.31; H, 6.69.
2,7-Di(3,5-dimethylphenyl)-9H-fluorene (8c)
1
Light yellow solid, m.p. 195–196 °C. H NMR (400 MHz, CDCl3, δ,
2-(3,5-Difluorophenyl)-9H-fluorene (7e)
ppm): 7.77 (d, J = 8.0 Hz, 2H, Ar-H), 7.71 (s, 2H, Ar-H), 7.55 (d,
J = 8 Hz, 1H, Ar-H), 7.22 (s, 4H, Ar-H), 3.94 (s, 2H, CH2), 2.35 (s, 12H,
CH3). 13C NMR (101 MHz, CDCl3, δ, ppm): 144.38 (Ar-C), 141.50 (Ar-
C), 140.55 (Ar-C), 140.07 (Ar-C), 138.27 (Ar-C), 128.79 (Ar-C), 126.09
(Ar-C), 125.12 (Ar-C), 123.81 (Ar-C), 120.04 (Ar-C), 37.05 (C, CH2),
21.45 (C, CH3). MS (ESI): m/z calcd for C29H25 [M ꢁ H]+ 373.2; found
373.3. Elemental analysis: calcd for C29H26 (%): C, 93.00; H, 7.00;
found (%): C, 93.02; H, 6.98.
1
Light yellow solid, m.p. 148–149 °C. H NMR (400 MHz, CDCl3, δ,
ppm): 7.83 (t, J = 7.3 Hz, 2H, Ar-H), 7.72 (s, 1H, Ar-H), 7.57 (dd,
J = 7.2, 4.2 Hz, 2H, Ar-H), 7.40 (d, J = 7.4 Hz, 1H, Ar-H), 7.35 (d,
J = 7.4 Hz, 1H, Ar-H), 7.17 (d, J = 7.6 Hz, 2H, Ar-H), 6.79 (s, 1H, Ar-
H), 3.95 (s, 2H, CH2). 13C NMR (101 MHz, CDCl3, δ, ppm): 164.61 (d,
J = 13.1 Hz, Ar-C), 162.15 (d, J = 13.2 Hz, Ar-C), 144.88 (t,
J = 9.5 Hz, Ar-C), 144.07 (Ar-C), 143.55 (Ar-C), 142.13 (Ar-C), 141.03
(Ar-C), 137.40 (Ar-C), 127.13 (Ar-C), 126.94 (Ar-C), 125.86 (Ar-C),
125.10 (Ar-C), 123.60 (Ar-C), 120.26 (Ar-C), 120.16 (Ar-C), 109.95 (d,
J = 7.1 Hz, Ar-C), 109.76 (d, J = 7.1 Hz, Ar-C), 102.24 (t, J = 25.5 Hz,
Ar-C), 36.96 (C, CH2). MS (ESI): m/z calcd for C19H11F2 [M ꢁ H]+
277.1; found 277.1. Elemental analysis: calcd for C19H12F2 (%): C,
82.00; H, 4.35; found (%): C, 82.05; H, 4.33.
2,7-Di(3,5-bis (trifluoromethyl)phenyl)-9H-fluorene (8d)
1
Yellow solid, m.p. 190–192 °C. H NMR (400 MHz, CDCl3, δ, ppm):
8.09 (s, 4H, Ar-H), 7.95 (d, J = 8.0 Hz, 2H, Ar-H), 7.86 (t, J = 12.0 Hz,
4H, Ar-H), 7.68 (dd, J1 = 8.0 Hz, J2 = 1.6 Hz, 2H, Ar-H), 4.10 (s, 2H,
CH2). 13C NMR (101 MHz, CDCl3, δ, ppm): 144.68 (Ar-C), 143.36 (Ar-
C), 141.57 (Ar-C), 137.26 (Ar-C), 132.16 (q, Ar-C), 127.17 (Ar-C),
126.41 (Ar-C), 124.76 (Ar-C), 124.02 (Ar-C), 122.05 (Ar-C), 122.10
(Ar-C), 122.84 (Ar-C), 37.05 (C, CH2). MS (ESI): m/z calcd for
C29H13F12 [M ꢁ H]+ 590.1; found 590.3. Elemental analysis: calcd
for C29H14F12 (%): C, 59.00; H, 2.39; found (%): C, 59.04; H, 2.36.
2-(3,4,5-Trifluorophenyl)-9H-fluorene (7f)
1
Light yellow solid, m.p. 188–190 °C. H NMR (400 MHz, CDCl3, δ,
ppm): 7.83 (d, J = 8.0 Hz, 2H, Ar-H), 7.65 (s, 1H, Ar-H), 7.58 (d,
J = 7.2 Hz, 1H, Ar-H), 7.50 (d, J = 8.0 Hz, 1H, Ar-H), 7.42 (t,
J = 7.4 Hz, 1H, Ar-H), 7.36 (t, J = 7.2 Hz, 1H, Ar-H), 7.30–7.19 (m,
2H, Ar-H), 3.94 (s, 2H, CH2). 13C NMR (101 MHz, CDCl3, δ, ppm):
152.73 (d, Ar-C), 152.63 (d, Ar-C), 150.25 (d, Ar-C), 150.15 (d, Ar-C),
144.12 (Ar-C), 143.47 (Ar-C), 140.88 (Ar-C), 137.64 (m, Ar-C), 136.58
(Ar-C), 127.17 (Ar-C), 126.94 (Ar-C), 125.88 (Ar-C), 125.09 (Ar-C),
123.41 (Ar-C), 120.28 (Ar-C), 120.14 (Ar-C), 111.00 (Ar-C), 110.94
(Ar-C), 110.84 (Ar-C), 110.78 (Ar-C), 36.91 (C, CH2). MS (ESI): m/z calcd
for C19H10F3 [M ꢁ H]+ 295.1; found 295.1. Elemental analysis: calcd
for C19H11F3 (%): C, 77.02; H, 3.74; found (%): C, 77.06; H, 3.70.
2,7-Bis(3,5-difluorophenyl)-9H-fluorene (8e)
1
Yellow solid, m.p. 185–187 °C. H NMR (400 MHz, CDCl3, δ, ppm):
7.85 (d, J = 8.0 Hz, 2H, Ar-H), 7.73 (s, 2H, Ar-H), 7.58 (d, J = 8.0 Hz,
2H, Ar-H), 7.19–7.14 (m, 4H, Ar-H), 7.83–6.77 (m, 2H, Ar-H), 3.99 (s,
2H, CH2). 13C NMR (101 MHz, CDCl3, δ, ppm): 164.50 (d, Ar-C),
162.13 (d, Ar-C), 144.64 (t, Ar-C), 144.37 (Ar-C), 141.35 (Ar-C),
137.79 (Ar-C), 126.05 (Ar-C), 123.67 (Ar-C), 120.56 (Ar-C), 109.87 (q,
Ar-C), 102.38 (t, Ar-C), 36.97 (C, CH2). MS (ESI): m/z calcd for
C25H13F4 [M ꢁ H]+ 390.1; found 390.2. Elemental analysis: calcd
for C25H14F4 (%): C, 76.92; H, 3.61; found (%): C, 76.96; H, 3.57.
4-(9H-Fluoren-2-yl)-N,N-diphenylaniline (7g)
1
Yellow solid, m.p. 195–196 °C. H NMR (400 MHz, CDCl3, δ, ppm):
2,7-Bis(3,4,5-trifluorophenyl)-9H-fluorene (8f)
7.79 (t, J = 8.2 Hz, 2H), 7.73 (s, 1H), 7.58 (d, J = 8.0 Hz, 1H, Ar-H),
7.53 (d, J = 7.8 Hz, 3H, Ar-H), 7.36 (t, J = 7.6 Hz, 1H, Ar-H), 7.31–
7.19 (m, 5H, Ar-H), 7.14 (dd, J = 8.2, 3.2 Hz, 6H, Ar-H), 7.02 (t,
1
Yellow solid, m.p. 198–199 °C. H NMR (400 MHz, CDCl3, δ, ppm):
7.86 (d, J = 8.0 Hz, 2H, Ar-H), 7.70 (s, 2H, Ar-H), 7.54 (d, J = 8.0 Hz,
Appl. Organometal. Chem. (2016)
Copyright © 2016 John Wiley & Sons, Ltd.
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