4930
Y. Zhang et al. / Tetrahedron 71 (2015) 4927e4932
4.2. Typical procedure for the palladium-catalyzed the cou-
pling reactions of aryl halides and phenols with K3PO4 as base
and toluene as solvent
7.74 (dd, J¼0.8, 8.0 Hz, 1H); 13C NMR (100 MHz, CDCl3):
d 120.8,
121.4, 121.9, 124.2, 126.38, 126.4, 130.1, 132.4, 149.2, 154.9, 172.1.
4.2.9. 3-Phenoxyquinoline (3fa).9a Yellow solid (71.3 mg, yield:
An oven-dried Schlenk tube was evacuated and backfilled with
nitrogen. The Schlenk tube was charged with Pd(bda)2 (11.5 mg,
0.02 mmol), L1 (13.7 mg, 0.03 mmol), K3PO4 (424.5 mg, 2 mmol),
and toluene (1.0 mL). After stirring for 15 min, the solution of aryl
halide (1.0 mmol) and phenol (1.2 mmol) in toluene (1.5 mL) was
added. The septum was replaced with an inside reflux condenser,
and then the reaction mixture was stirred for 18 h at 110 ꢀC. Then,
the reaction mixture was cooled to room temperature and
quenched with water (5 mL). After separating the organic phase,
the aqueous phase was extracted with ethyl acetate (3 mLꢁ3), and
the combined organic phase was dried over anhydrous Na2SO4. The
solvent was concentrated under reduced pressure, and then the
crude material was purified by column chromatography on
silica gel.
32%), mp: 62e65 ꢀC. 1H NMR (400 MHz, CDCl3):
d 7.10e7.12 (m, 2H),
7.19e7.23 (m, 1H), 7.39e7.44 (m, 2H), 7.52e7.54 (m, 2H), 7.61e7.65
(m, 1H), 7.68 (dd, J¼1.2, 8.0 Hz, 1H), 8.10 (d, J¼8.4 Hz, 1H), 8.82 (d,
J¼2.8 Hz, 1H); 13C NMR (100 MHz, CDCl3):
d 119.3, 120.1. 124.3,
127.0, 127.3, 127.9, 128.6, 129.3, 130.1, 144.7, 145.2, 151.1, 156.2.
4.2.10. Ethyl 3-phenoxybenzoate (3ga).16 Colorless oil (49.3 mg,
yield: 21%). 1H NMR (400 MHz, CDCl3):
d
1.37 (t, J¼7.2, 3H), 4.36 (q,
J¼7.2 Hz, 2H), 7.00e7.23 (m, 2H), 7.13 (t, J¼7.2 Hz,1H), 7.20e7.21 (m,
1H), 7.33e7.42 (m, 3H), 7.68e7.69 (m, 1H), 7.78 (td, J¼1.2, 7.6 Hz,
1H); 13C NMR (100 MHz, CDCl3):
d 14.4, 61.3, 119.1, 119.8, 123.3,
123.8, 124.4, 129.8, 130.0, 132.4, 156.9, 157.4, 166.1.
4.2.11. 2-Phenoxynaphthalene (3ha).3d Pale red solid (85.8 mg,
yield: 39%), mp: 47e48 ꢀC. 1H NMR (400 MHz, CDCl3):
d 7.05e7.09
4.2.1. 4-Phenoxybenzonitrile (3aa).12 Yellow solid (195.1 mg, yield:
(m, 2H), 7.14e7.18 (m,1H), 7.28 (dd, J¼2.4, 8.8 Hz,1H), 7.30e7.49 (m,
99%), mp: 42e46 ꢀC. 1H NMR (400 MHz, CDCl3):
d 6.99e7.02 (m,
5H), 7.69 (d, J¼8.4 Hz, 1H), 7.80e7.83 (m, 2H); 13C NMR (100 MHz,
2H), 7.06e7.08 (m, 2H), 7.23 (t, J¼7.2 Hz, 1H), 7.40e7.44 (m, 2H),
CDCl3): d 114.2, 119.3, 120.1, 123.6,124.8,126.6,127.9, 129.96,130.00,
7.58e7.62 (m, 2H); 13C NMR (100 MHz, CDCl3):
d
105.7, 117.9, 118.9,
130.3, 134.4, 155.2, 157.3.
120.4, 125.2, 130.2, 134.1, 154.8, 161.6.
4.2.12. Bis(2-methylphenyl)ether (3je).17 When 2-methyl bromo-
benzene was used, the product was obtained as pale yellow oil
(194.6 mg, yield: 97%). When 2-methyl chlorobenzene was used,
the product was obtained (180.7 mg, yield: 93%). 1H NMR
4.2.2. 4-Phenoxyacetophenone (3ba).13 Yellow solid (202.1 mg,
yield: 94%), mp: 50e52 ꢀC. 1H NMR (400 MHz, CDCl3):
2.57 (s, 3H),
d
6.99e7.01 (m, 2H), 7.06e7.08 (m, 2H), 7.18e7.22 (m, 1H), 7.38e7.42
(m, 2H), 7.93e7.95 (m, 2H); 13C NMR (100 MHz, CDCl3):
d
26.7, 117.4,
(400 MHz, CDCl3):
d
2.31 (s, 6H), 6.74 (dd, J¼0.8, 8.0 Hz, 2H), 7.02
120.3, 124.7, 129.7, 130.8, 132.0, 155.6, 162.1, 196.9.
(td, J¼0.8, 7.2 Hz, 2H), 7.11e7.13 (m, 2H), 7.25e7.27 (m, 2H); 13C
NMR (100 MHz, CDCl3): d 16.3, 117.8, 123.1, 127.1, 128.9, 131.4, 155.3.
4.2.3. 1-Phenoxy-4-(trifluoromethyl)benzene (3ca).14 Colorless oil
(203.1 mg, yield: 86%). 1H NMR (400 MHz, CDCl3):
d
7.04e7.07 (m,
4.2.13. 4-tert-Butyl-20-methyldiphenyl ether (3ie).6a When 2-
methyl bromobenzene was used, the product was obtained as
colorless oil (231.2 mg, yield: 96%). When 2-methyl chlorobenzene
was used, the product was obtained (205.0 mg, yield: 86%). 1H NMR
(400 MHz, CDCl3): 1.32 (s, 9H), 2.27 (s, 3H), 6.84e6.87 (m, 2H), 6.90
(d, J¼8.0 Hz, 1H), 7.05 (dt, J¼0.8, 7.6 Hz, 1H), 7.14 (td, J¼1.6, 7.6 Hz,
1H), 7.24e7.29 (m, 1H), 7.30e7.33 (m, 2H); 13C NMR (100 MHz,
4H), 7.18e7.22 (m,1H), 7.38e7.42 (m, 2H), 7.57 (d, J¼8.8 Hz, 2H); 13
C
NMR (100 MHz, CDCl3):
130.2, 155.9, 160.7.
d 118.0, 120.1, 124.6, 124.8, 125.7, 127.2,
4.2.4. Ethyl 4-phenoxybenzoate (3da).3d Pale yellow oil (234.3 mg,
yield: 97%). 1H NMR (400 MHz, CDCl3):
d
1.38 (t, J¼7.2 Hz, 3H), 4.36
(q, J¼7.2 Hz, 2H), 6.97e7.00 (m, 2H), 7.04e7.08 (m, 2H), 7.16e7.21
CDCl3): d 16.4, 31.7, 34.4, 117.1, 119.5, 123.8, 126.6, 127.2, 139.9, 131.5,
145.3, 155.0, 155.6.
(m, 1H), 7.37e7.41 (m, 2H), 7.99e8.03 (m, 2H); 13C NMR (100 MHz,
CDCl3):
166.2.
d 14.6, 61.0,117.4,120.1,124.5,125.0,130.1,131.7,155.8,161.8,
4.2.14. 1-(tert-Butyl)-2-(4-(tert-butyl)phenoxy)benzene (3if). Color-
less oil (273.9 mg, yield: 96%). 1H NMR (400 MHz, CDCl3):
d 1.31 (s,
4.2.5. Methyl 4-(4-cyanophenoxy)benzoate (3ab).15 Colorless oil
(228.8 mg, yield: 92%). 1H NMR (400 MHz, CDCl3):
3.92 (s, 3H),
7.07e7.10 (m, 4H), 7.64e7.67 (m, 2H), 8.06e8.10 (m, 2H); 13C NMR
(100 MHz, CDCl3): 52.4, 107.2, 118.6, 119.2, 119.3, 126.6, 132.1,
9H),1.42 (s, 9H), 6.82 (d, J¼8.0 Hz,1H), 6.91 (d, J¼8.8 Hz, 2H), 7.02 (t,
d
J¼7.6 Hz, 1H), 7.11 (t, J¼7.6 Hz, 1H), 7.33 (d, J¼8.8 Hz, 2H), 7.38 (d,
J¼7.6 Hz, 1H); 13C NMR (100 MHz, CDCl3):
d 30.2, 31.7, 34.4, 34.9,
d
118.6, 119.8, 122.9, 126.6, 127.1, 127.2, 140.7, 145.6, 155.3, 156.5. IR
(cmꢂ1): 3073, 2960, 2868, 1596, 1575, 1510, 1483, 1439, 1363, 1234,
1198, 1129, 1108, 1088, 1051, 881, 853, 746. HRMS m/z calcd for
134.5, 159.3, 160.3, 166.3.
4.2.6. 4-(4-Methoxyphenoxy)benzonitrile (3ac).9d Pale yellow oil
C
20H26ONa [MþNa]þ: 305.1881, found: 305.1881.
(221.9 mg, 98%). 1H NMR (400 MHz, CDCl3):
d
3.85 (s, 3H),
6.94e6.99 (m, 4H), 7.01e7.05 (m, 2H), 7.58e7.61 (m, 2H); 13C NMR
4.2.15. Ethyl 3-(o-tolyloxy)benzoate (3ge). Colorless oil (214.3 mg,
yield: 85%). 1H NMR (400 MHz, CDCl3):
(100 MHz, CDCl3):
148.0, 157.1, 162.6.
d
55.8, 105.4, 115.4, 117.3, 119.1, 122.0, 134.2,
d
1.37 (t, J¼7.2 Hz, 3H), 2.23
(s, 3H), 4.35 (q, J¼7.2 Hz, 2H), 6.90 (d, J¼8.0 Hz, 1H), 7.06e7.11 (m,
2H), 7.16e7.21 (m, 1H), 7.25e7.28 (m, 1H), 7.35 (t, J¼8.0 Hz, 1H), 7.58
(dd, J¼1.6, 2.4 Hz, 1H), 7.72e7.74 (m, 1H); 13C NMR (100 MHz,
4.2.7. 4-(o-Tolyloxy)benzonitrile (3ad).9d Colorless oil (206.4 mg,
yield: 98%). 1H NMR (400 MHz, CDCl3):
2.17 (s, 3H), 6.90e6.92 (m,
d
CDCl3): d 14.4, 16.3, 61.2, 118.3, 119.9, 121.7, 123.6, 124.5, 127.4, 129.7,
2H), 6.98 (dd, J¼1.2, 7.6 Hz, 1H), 7.17 (td, J¼1.2 Hz, 7.6 Hz, 1H), 7.23
130.1, 131.7, 132.3, 154.1, 158.0, 166.3. IR (cmꢂ1): 3068, 3027, 2981,
1721, 1580, 1484, 1442, 1272, 1234, 1202, 1180, 1112, 1098, 1075,
1023, 943, 754. HRMS m/z calcd for C16H17O3 [MþH]þ: 257.1178,
found: 257.5195.
(dd, J¼1.6, 7.6 Hz, 1H), 7.29 (dd, J¼1.6, 7.6 Hz, 1H), 7.56e7.59 (m,
2H); 13C NMR (100 MHz, CDCl3):
d 16.1, 105.3, 116.8, 119.0, 121.1,
125.8, 127.7, 130.6, 132.0, 134.2, 152.4, 161.8.
4.2.8. 2-Phenoxybenzo[d]thiazole (3ea).13 Colorless oil (199.1 mg,
4.2.16. 3-(2-(tert-Butyl)phenoxy)quinoline
(262.9 mg, yield: 93%), mp 87e91 ꢀC. 1H NMR (400 MHz, CDCl3):
1.44 (s, 9H), 6.91 (dd, J¼1.6, 7.6 Hz, 1H), 7.13e7.23 (m, 2H),
(3ff). Yellow
solid
yield: 86%). 1H NMR (400 MHz, CDCl3):
d
7.27e7.33 (m, 2H),
7.36e7.41 (m, 3H), 7.44e7.48 (m, 2H), 7.67 (dd, J¼0.8, 8.0 Hz, 1H),
d