13
m, ArH), 7.29-7.37 (6H, m, ArH), 7.92-7.95 (1H, m, ArH); 13C-
NMR (100 MHz, CDCl3) δ 38.2 (CH2), 49.6 (CH2), 55.4 (CH2),
113.6 (CH), 117.1 (CH), 119.9 (C), 126.9 (2 x CH), 127.6 (CH),
128.4 (CH), 129.0 (2 x CH), 135.6 (CH), 137.4 (C), 151.9 (C),
193.7 (C). The spectral data of 46 were consistent with the
literature data.27
2. Heck, R. F., Palladium-Catalyzed Vinylation of Organic
ACCEPTED MANUSCRIPT
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4.2.25. Scheme 4; Reaction B.
44 (0.183 g, 0.5 mmol) was treated with 11 (10 mg, 0.05
mmol, 0.1 equiv), KOtBu (0.168 g, 1.5 mmol, 3 equiv) and
anhydrous DMSO (2 mL) under the general reaction procedure at
RT overnight. Reaction mixture was quenched with saturated
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aqueous
ammonium
chloride
and
extracted
with
dichloromethane. Purification (2% - 25% ethyl acetate in hexane)
to yield 2-phenylquinolin-4(1H)-one 47 (32.4 mg, 27%) as a
yellow solid, 1-benzyl-2,3-dihydroquinolin-4(1H)-one 46 (25.2
mg, 21%) as a yellow oil and 1-(2-(methylamino)phenyl)ethan-1-
one 48 (9.5 mg, 13%) as a yellow oil.
For 5-methyl-6,11-dihydrodibenzo[b,f]azocin-12(5H)-one, 47;
m.p. 102-106 C (lit. 13: 108-109 C); [Found: (GC-CI+) 238.1];
o
o
νmax(film) / cm-1 1661, 1591, 1487, 1350, 1285, 1163, 1088,
1
1009, 756, 735, 623; H-NMR (400 MHz, CDCl3) δ 3.01 (3H, s,
CH3), 4.08 (2H, s, CH2), 4.22 (2H, s, CH2), 6.90-6.94 (1H, m,
ArH), 7.05 (1H, d, J = 8.4 Hz, ArH), 7.11 (1H, d, J = 7.6 Hz,
ArH), 7.21-7.29 (3H, m, ArH), 7.40-7.45 (1H, m, ArH), 7.61
(1H, dd, J = 7.6, 1.6 Hz, ArH); 13C-NMR (100 MHz, CDCl3) δ
38.0 (CH3), 48.3 (CH2), 64.6 (CH2), 115.2 (CH), 119.0 (CH),
127.2 (CH), 128.4 (CH), 128.8 (CH), 129.5 (CH), 130.9 (CH),
131.2 (C), 132.7 (CH), 135.3 (C), 135.8 (C) 153.0 (C), 210.9 (C).
The spectral data of 47 were consistent with the literature data.13
o
For 1-(2-(methylamino)phenyl)ethan-1-one 48; m.p. 45-47 C
(lit.28: 37-39 C); [Found: (HRMS-ESI+) 150.0910. C9H12NO+
o
(M+H)+ requires 150.0913]; νmax(film) / cm-1 3321, 1632, 1562,
1516, 1410, 1234, 1165, 951, 743, 652, 613; 1H-NMR (400 MHz,
CDCl3) δ 2.57 (3H, s, CH3), 2.91 (3H, d, J = 4.8 Hz, CH3), 6.57-
6.61 (1H, m, ArH), 6.68-6.70 (1H, m, ArH), 7.36-7.40 (1H, m,
ArH), 7.73-7.75 (1H, d, J = 8, 1.6 Hz, ArH), 8.78 (1H, br s, NH);
13C-NMR (100 MHz, CDCl3) δ 27.9 (CH3), 29.3 (CH3), 111.3
(CH), 113.9 (CH), 117.6 (C), 132.7 (CH), 135.1 (CH), 152.0 (C),
200.8 (C). The spectral data of 48 were consistent with the
literature data.28
4.2.26. Reaction of 47 with KOtBu
47 (0.010 g, 0.042 mmol) was treated with KOtBu (0.014 g,
0.126 mmol, 3 equiv) and anhydrous benzene (1 mL) under the
o
general reaction procedure at 120 C for 1 h. Reaction mixture
was quenched with water and extracted with ethyl acetate. To the
crude reaction mixture was added 1,3,5-trimethoxybenzene
(0.025 mmol) as an internal standard. The yields were deduced
from NMR analysis to be yield ((4bR,9bS)-5-methyl-4b,10-
dihydroindeno[1,2-b]indol-9b(5H)-yl)oxonium 45 (31%) and
starting material 47 (29%).
5. Acknowledgements
We thank the EPSRC and University of Strathclyde for the
funding and the National Crystallography Service, University of
Southampton, for data collection on compound 45. High
Resolution mass spectrometry data were acquired at the EPSRC
National Mass Spectrometry Service Centre, Swansea.
6. References and Notes
1. Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.;
Snieckus, V., Angew. Chem., Int. Ed. 2012, 51, 5062−5085.