H. Doucet et al.
1
affords 22 (0.212 g, 78%). 1H NMR (200 MHz, CDCl3): d=7.97 (d,
J=8.2 Hz, 1H), 7.95 (d, J=8.2 Hz, 1H), 7.79 (d, J=8.2 Hz, 1H),
7.62–7.05 (m, 8H), 2.74 (q, J=7.5 Hz, 2H), 1.30 ppm (t, J=7.5 Hz,
3H). 13C NMR (50 MHz, CDCl3): d=156.9, 154.3, 135.3, 134.2, 132.9,
130.6, 128.7, 128.6, 128.5, 126.5, 126.4, 126.3, 126.0, 123.9, 122.9,
120.5, 115.0, 111.2, 20.9, 13.2 ppm. Elemental analysis: calcd (%) for
C20H16O (272.34): C 88.20, H 5.92; found: C 88.14, H 5.99.
0.001 mmol) affords 29 (0.217 g, 78%). H NMR (200 MHz, CDCl3):
d=10.10 (s, 1H), 8.03 (d, J=8.3 Hz, 2H), 7.69 (d, J=8.3 Hz, 2H),
7.64–7.48 (m, 2H), 7.40–7.25 (m, 2H), 2.91 (t, J=7.5 Hz, 2H), 1.80
(quint., J=7.5 Hz, 2H), 1.44 (sext., J=7.5 Hz, 2H), 0.94 ppm (t, J=
7.5 Hz, 3H). 13C NMR (50 MHz, CDCl3): d=191.7, 156.3, 154.0,
139.5, 134.8, 130.1, 129.3, 128.0, 123.9, 122.8, 119.1, 115.9, 111.0,
30.3, 26.6, 22.4, 13.7 ppm. Elemental analysis: calcd (%) for C19H18O2
(278.35): C 81.99, H 6.52; found: C 81.87, H 6.70.
3-(2-Ethylbenzofuran-3-yl)-pyridine 24: The reaction of 3-bromopyr-
idine (0.158 g, 1 mmol), 2-ethylbenzofuran (0.292 g, 2 mmol), and
KOAc (0.196 g, 2 mmol) with Pd(OAc)2 (0.23 mg, 0.001 mmol) af-
1-[3-(2-Butyl-benzofuran-3-yl)-phenyl]-ethanone 30: The reaction of
3-bromoacetophenone (0.199 g, 1 mmol), 2-n-butylbenzofuran
(0.348 g, 2 mmol), and KOAc (0.196 g, 2 mmol) with Pd(OAc)2
(0.23 mg, 0.001 mmol) affords 30 (0.210 g, 72%). 1H NMR
(200 MHz, CDCl3): d=8.16 (s, 1H), 7.95 (d, J=8.3 Hz, 1H), 7.73–
7.40 (m, 4H), 7.38–7.25 (m, 2H), 2.86 (t, J=7.5 Hz, 2H), 2.69 (s, 3H),
1.80 (quint., J=7.5 Hz, 2H), 1.45 (sext., J=7.5 Hz, 2H), 0.92 ppm (t,
J=7.5 Hz, 3H). 13C NMR (50 MHz, CDCl3): d=197.8, 155.7, 153.9,
137.6, 133.6, 133.5, 129.0, 128.8, 128.4, 126.9, 123.7, 122.7, 119.1,
116.0, 110.9, 30.4, 26.7, 26.5, 22.4, 13.7 ppm. Elemental analysis:
calcd (%) for C20H20O2 (292.37): C 82.16, H 6.89; found: C 82.24, H
6.74.
1
fords 24 (0.187 g, 84%). H NMR (200 MHz, CDCl3): d=8.78 (s, 1H),
8.65 (d, J=4.0 Hz, 1H), 7.83 (d, J=6.5 Hz, 1H), 7.62–7.40 (m, 3H),
7.36–7.25 (m, 2H), 2.90 (q, J=7.5 Hz, 2H), 1.41 ppm (t, J=7.5 Hz,
3H). 13C NMR (50 MHz, CDCl3): d=157.0, 154.1, 149.8, 148.2, 136.2,
128.3, 123.9, 123.6, 122.8, 118.9, 112.9, 111.0, 20.2, 12.9 ppm. Ele-
mental analysis: calcd (%) for C15H13NO (223.27): C 80.69, H 5.87;
found: C 80.68, H 5.69.
4-(2-Ethylbenzofuran-3-yl)-pyridine 25: The reaction of 4-bromopyr-
idine hydrochloride (0.195 g, 1 mmol), 2-ethylbenzofuran (0.292 g,
2 mmol), and KOAc (0.196 g, 2 mmol) with PdCl(C3H5)(dppb) (3 mg,
1
2-Butyl-3-(1-naphtyl)-benzofuran 31: The reaction of 1-bromonaph-
thalene (0.207 g, 1 mmol), 2-n-butylbenzofuran (0.348 g, 2 mmol),
and KOAc (0.196 g, 2 mmol) with Pd(OAc)2 (0.23 mg, 0.001 mmol)
affords 31 (0.222 g, 74%). 1H NMR (200 MHz, CDCl3): d=7.97 (d,
J=8.2 Hz, 1H), 7.95 (d, J=8.2 Hz, 1H), 7.79 (d, J=8.2 Hz, 1H),
7.62–7.05 (m, 8H), 2.76 (t, J=7.5 Hz, 2H), 1.75 (quint., J=7.5 Hz,
2H), 1.45 (sext., J=7.5 Hz, 2H), 0.92 ppm (t, J=7.5 Hz, 3H).
13C NMR (50 MHz, CDCl3): d=156.4, 153.9, 144.2, 133.8, 132.5,
130.2, 128.3, 128.2, 128.1, 126.1, 125.9, 125.8, 125.5, 123.4, 122.4,
120.0, 115.2, 110.7, 30.2, 26.6, 22.3, 13.7 ppm. Elemental analysis:
calcd (%) for C22H20O (300.39): C 87.96, H 6.71; found: C 87.10, H
6.81.
0.005 mmol) affords 25 (0.147 g, 66%). H NMR (200 MHz, CDCl3):
d=8.72 (m, 2H), 7.66–7.40 (m, 4H), 7.36–7.25 (m, 2H), 2.93 (q, J=
7.5 Hz, 2H), 1.41 ppm (t, J=7.5 Hz, 3H). 13C NMR (50 MHz, CDCl3):
d=157.7, 154.1, 149.9, 141.4, 127.5, 124.2, 123.6, 123.1, 119.1,
113.9, 111.2, 20.4, 12.8 ppm. Elemental analysis: calcd (%) for
C15H13NO (223.27): C 80.69, H 5.87; found: C 80.54, H 5.98.
3-(2-Ethylbenzofuran-3-yl)-quinoline 26: The reaction of 3-bromo-
quinoline (0.208 g, 1 mmol), 2-ethylbenzofuran (0.292 g, 2 mmol),
and KOAc (0.196 g, 2 mmol) with Pd(OAc)2 (0.23 mg, 0.001 mmol)
affords 26 (0.183 g, 67%). 1H NMR (200 MHz, CDCl3): d=9.10 (d,
J=1.8 Hz, 1H), 8.27 (d, J=1.8 Hz, 1H), 8.20 (d, J=8.0 Hz, 1H), 7.91
(d, J=8.0 Hz, 1H), 7.79 (t, J=7.7 Hz, 1H), 7.70–7.50 (m, 3H), 7.40–
7.25 (m, 2H), 2.97 (q, J=7.5 Hz, 2H), 1.44 ppm (t, J=7.5 Hz, 3H).
13C NMR (50 MHz, CDCl3): d=157.4, 154.1, 150.9, 146.8, 135.3,
129.6, 129.1, 128.4, 128.1, 127.7, 127.1, 126.2, 124.1, 122.9, 119.0,
113.5, 111.1, 20.4, 13.0 ppm. Elemental analysis: calcd (%) for
C19H15NO (273.33): C 83.49, H 5.53; found: C 83.38, H 5.41.
3-(2-Butylbenzofuran-3-yl)-quinoline 32: The reaction of 3-bromo-
quinoline (0.208 g, 1 mmol), 2-n-butylbenzofuran (0.348 g, 2 mmol),
and KOAc (0.196 g, 2 mmol) with Pd(OAc)2 (0.23 mg, 0.001 mmol)
affords 32 (0.211 g, 70%). 1H NMR (200 MHz, CDCl3): d=9.10 (d,
J=1.8 Hz, 1H), 8.27 (d, J=1.8 Hz, 1H), 8.21 (d, J=8.0 Hz, 1H), 7.91
(d, J=8.0 Hz, 1H), 7.79 (t, J=7.7 Hz, 1H), 7.70–7.50 (m, 3H), 7.40–
7.25 (m, 2H), 2.94 (t, J=7.5 Hz, 2H), 1.84 (quint., J=7.5 Hz, 2H),
1.45 (sext., J=7.5 Hz, 2H), 0.94 ppm (t, J=7.5 Hz, 3H). 13C NMR
(50 MHz, CDCl3): d=156.4, 154.1, 151.1, 147.0, 135.1, 129.4, 129.3,
128.4, 128.0, 127.7, 127.0, 126.2, 123.9, 122.9, 118.9, 113.5, 111.1,
30.4, 26.6, 22.4, 13.7 ppm. Elemental analysis: calcd (%) for
C21H19NO (301.28): C 83.69, H 6.35; found: C 83.50, H 6.40.
4-(2-Ethylbenzofuran-3-yl)-isoquinoline 27: The reaction of 4-bro-
moisoquinoline (0.208 g, 1 mmol), 2-ethylbenzofuran (0.292 g,
2 mmol), and KOAc (0.196 g, 2 mmol) with Pd(OAc)2 (0.45 mg,
1
0.002 mmol) affords 27 (0.167 g, 61%). H NMR (200 MHz, CDCl3):
d=9.35 (s, 1H), 8.56 (s, 1H), 8.12 (m, 1H), 7.70–7.42 (m, 3H), 7.57
(d, J=8.0 Hz, 1H), 7.40–7.25 (m, 2H), 7.17 (d, J=8.0 Hz, 1H), 2.77
(q, J=7.5 Hz, 2H), 1.32 ppm (t, J=7.5 Hz, 3H). 13C NMR (50 MHz,
CDCl3): d=158.1, 154.1, 152.3, 143.9, 135.2, 130.6, 129.8, 128.0,
127.4, 125.1, 123.8, 122.7, 119.7, 111.2, 111.0, 20.4, 12.9 ppm. Ele-
mental analysis: calcd (%) for C19H15NO (273.33): C 83.49, H 5.53;
found: C 83.56, H 5.60.
1-(3-Pyridin-3-ylbenzofuran-2-yl)-ethanone 33: The reaction of 3-
bromopyridine (0.158 g, 1 mmol), 2-acetylbenzofuran (0.320 g,
2 mmol), and KF (0.116 g, 2 mmol) with PdCl(C3H5)(dppb) (3 mg,
1
0.005 mmol) affords 33 (0.069 g, 29%). H NMR (200 MHz, CDCl3):
d=8.65–8.48 (m, 2H), 7.75–7.20 (m, 6H), 4.27 ppm (s, 3H). 13C NMR
(50 MHz, CDCl3): d=187.3, 155.6, 151.8, 150.5, 148.4, 137.0, 129.3,
128.5, 126.8, 124.0, 123.4, 123.3, 113.6, 112.3, 42.5 ppm. Elemental
analysis: calcd (%) for C15H11NO2 (237.25): C 75.94, H 4.67; found: C
75.90, H 4.49.
5-(2-Ethylbenzofuran-3-yl)-pyrimidine 28: The reaction of 5-bromo-
pyrimidine (0.159 g, 1 mmol), 2-ethylbenzofuran (0.292 g, 2 mmol),
and KOAc (0.196 g, 2 mmol) with Pd(OAc)2 (0.23 mg, 0.001 mmol)
affords 28 (0.157 g, 70%). 1H NMR (200 MHz, CDCl3): d=9.26 (s,
1H), 8.92 (s, 2H), 7.60–7.50 (m, 2H), 7.40–7.25 (m, 2H), 2.93 (q, J=
7.5 Hz, 2H), 1.41 ppm (t, J=7.5 Hz, 3H). 13C NMR (50 MHz, CDCl3):
d=157.8, 157.2, 156.4, 154.2, 127.5, 124.4, 123.2, 118.6, 115.7, 111.3,
109.6, 20.3, 12.9 ppm. Elemental analysis: calcd (%) for C14H12N2O
(224.26): C 74.98, H 5.39; found: C 74.92, H 5.47.
4-(2-Formylbenzofuran-3-yl)-benzonitrile 34: The reaction of 4-bro-
mobenzonitrile (0.182 g, 1 mmol), 2-formylbenzofuran (0.219 g,
1.5 mmol), and KOAc (0.192 g, 2 mmol) with Pd(OAc)2 (0.23 mg,
1
0.001 mmol) affords 34 (0.126 g, 51%). H NMR (200 MHz, CDCl3):
d=9.93 (s, 1H), 7.91 (d, J=8.3 Hz, 2H), 7.81 (d, J=8.3 Hz, 2H),
7.75–7.60 (m, 3H), 7.47 ppm (t, J=7.8 Hz, 1H). 13C NMR (50 MHz,
CDCl3): d=179.4, 155.4, 147.6, 134.1, 132.8, 130.9, 130.6, 130.0,
126.4, 124.8, 122.1, 118.2, 113.2, 113.1 ppm. Elemental analysis:
4-(2-Butylbenzofuran-3-yl)-benzaldehyde 29: The reaction of 4-bro-
mobenzaldehyde (0.185 g, 1 mmol), 2-n-butylbenzofuran (0.348,
2 mmol), and KOAc (0.196 g, 2 mmol) with Pd(OAc)2 (0.23 mg,
374
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ChemSusChem 2010, 3, 367 – 376