European Journal of Organic Chemistry
10.1002/ejoc.201900510
FULL PAPER
1
.5 Hz), 135.9 (d, J = 11.7 Hz), 134.4 (d, J = 97.6 Hz), 133.9 (d, J
15 min, 300 W, closed vessel). Purification of the crude material
by silica gel column chromatography (petroleum ether/ethyl
acetate, 100:0 to 50:50) furnished the product 3cc (65.8 mg, 61%)
as a light yellow oily compound, [TLC control (petroleum
=
96.8 Hz), 133.8 (q, J = 1.5 Hz), 128.4, 128.1 (d, J = 1.5 Hz),
1
4
2
27.9 (d, J = 1.5 Hz), 122.6, 120.5, 109.8, 82.7 (d, J = 3.0 Hz),
4.7 (d, J = 3.7 Hz), 39.5 (d, J = 67.4 Hz), 26.0 (d, J = 2.5 Hz),
1.3, 21.2 ppm. 31P NMR (CDCl
3
, 162 MHz): δ=27.96 ppm. HR-
ether/ethyl acetate 80:20), R
f
f
(1c)=0.9, R (3cc)=0.1, UV detection].
+
+
-1
MS (ESI+) m/z calculated for [C26
found 405.1996.
H
30
O
2
P] =[M+H] : 405.1978;
IR (MIR-ATR, 4000–600 cm ): max=3406, 2961, 2926, 1604,
-1 1
1487, 1249, 1109, 975, 807, 654 cm . H NMR (CDCl , 400 MHz):
3
δ=7.36 (d, J = 2.0 Hz, 1H, Ar–H), 7.33 (d, J = 2.0 Hz, 1H, Ar–H),
7.25 (d, J = 2.0 Hz, 1H, Ar–H), 7.09 (d, J = 2.0 Hz, 1H, Ar–H),
(
3,5-dimethyl-2,3-dihydro-1-benzofuran-3-yl)[bis(3,5-
dimethylphenyl)]phosphine oxide (3bc): GP was carried out
with 2-iodo-4-methyl-1-[(2-methylprop-2-enyl)oxy]benzene 1b
7.06 (d, J = 2.0 Hz, 1H, Ar–H), 6.90 (d, J = 2.0 Hz, 1H, Ar–H),
6.88 (dd, J = 7.83 and 2.0 Hz, 1H, Ar–H), 4.66 (d, J = 9.3 Hz, 1H,
(
(
72 mg, 0.25 mmol), bis(3,5-dimethylphenyl)phosphine oxide 2c
64.5 mg, 0.25 mmol), Pd (dba) (11.4 mg, 5 mol%), K CO (103.9
OCH ), 2.83–2.49 (m, 2H,
A
H ), 4.20 (d, J = 9.3 Hz, 1H, OCH H
B
B
A
2
3
2
3
CH ), 2.48 (q, J = 7.8 Hz, 1H, Ar–CH –CH ), 2.33 (s, 6H, 2 × CH ),
2
2
3
3
mg, 0.75 mmol) DMF (0.5 mL), under microwave irradiation (120
C, 15 min, 300 W, closed vessel). Purification of the crude
2.29 (s, 6H, 2 × CH ), 1.45 (s, 3H, CH ), 1.15 (t, J = 7.8 Hz, 1H,
3
3
) ppm. 13C NMR (CDCl
, 100 MHz): δ=156.9, 138.3
Ar–CH
2
–CH
3
3
material by silica gel column chromatography (petroleum
(d, J = 5.1 Hz), 138.2 (d, J = 5.1 Hz), 136.5, 135.6 (d, J = 11.0 Hz),
134.6 (d, J = 97.6 Hz), 134.0 (d, J = 96.8 Hz), 133.2 (d, J = 2.5
Hz), 128.0 (d, J = 9.4 Hz), 127.9 (d, J = 9.4 Hz), 127.5, 122.1,
109.4, 83.1 (d, J = 4.4 Hz), 44.8 (d, J = 4.4 Hz), 39.4 (d, J = 67.9
Hz), 28.2, 25.7 (d, J = 2.5 Hz), 21.3, 21.2, 15.9 ppm. 31P NMR
ether/ethyl acetate, 100:0 to 50:50) furnished the product 3bc
(
(
64.7 mg, 62%) as a light yellow oily compound, [TLC control
petroleum ether/ethyl acetate 80:20), R (1e)=0.9, R (3bc)=0.1,
f
f
-1
UV detection]. IR (MIR-ATR, 4000–600 cm ): max=3393, 2923,
-
1 1
1
710, 1485, 1225, 1185, 1109, 1026, 914, 806, 720, 659 cm . H
NMR (CDCl , 400 MHz): δ=7.35 (d, J = 1.0 Hz, 1H, Ar–H), 7.32
d, J = 1.0 Hz, 1H, Ar–H), 7.27 (d, J = 1.0 Hz, 1H, Ar–H), 7.24 (d,
J = 1.0 Hz, 1H, Ar–H), 7.08 (d, J = 1.0 Hz, 1H, Ar–H), 7.05 (d, J =
.0 Hz, 1H, Ar–H), 6.90–6.76 (m, 2H), 6.64 (d, J = 7.8 Hz, 1H, Ar–
H), 4.66 (d, J = 9.3 Hz, 1H, OCH ), 4.18 (d, J = 9.3 Hz, 1H,
OCH ), 2.72 (dd, J = 15.2 and 11.2 Hz, 1H), 2.59 (dd, J = 15.2
and 11.2 Hz, 1H), 2.32 (s, 6H, 2 × CH ), 2.28 (s, 6H, 2 × CH ),
.17 (s, 3H, CH ), 1.44 (s, 3H, CH , 100
) ppm. 13C NMR (CDCl
MHz): δ=156.7, 138.3 (d, J = 4.4 Hz), 138.2 (d, J = 4.4 Hz), 135.4
d, J = 11.0 Hz), 134.6 (d, J = 96.8 Hz), 134.0 (d, J = 96.8 Hz),
(CDCl
3
, 162 MHz): δ=28.01 ppm. HR-MS (ESI+) m/z calculated
+
]+: 450.2556; found 450.2562.
for [C28
H37NO
2
P] =[M+NH
4
3
(
(5-tert-butyl-3-methyl-2,3-dihydro-1-benzofuran-3-yl)[bis(3,5-
dimethylphenyl)]phosphine oxide (3dc): GP was carried out
with 4-tert-butyl-2-iodo-1-[(2-methylprop-2-enyl)oxy]benzene 1d
(82 mg, 0.25 mmol), bis(3,5-dimethylphenyl)phosphine oxide 2c
1
A
H
B
A
H
B
2 3 2 3
(64.5 mg, 0.25 mmol), Pd (dba) (11.4 mg, 5 mol%), K CO (103.9
3
3
2
3
3
3
mg, 0.75 mmol) DMF (0.5 mL), under microwave irradiation (120
C, 15 min, 300 W, closed vessel). Purification of the crude
material by silica gel column chromatography (petroleum
ether/ethyl acetate, 100:0 to 50:50) furnished the product 3dc
(81.1 mg, 71%) as a light yellow oily compound, [TLC control
(
1
9
3
33.2 (d, J = 2.0 Hz), 128.7, 128.0 (d, J = 8.9 Hz), 127.7 (d, J =
.4 Hz), 123.4, 109.3, 83.1 (d, J = 3.9 Hz), 44.8 (d, J = 3.7 Hz),
9.4 (d, J = 67.9 Hz), 25.7 (d, J = 2.5 Hz), 21.3, 21.2, 20.7 ppm.
(petroleum ether/ethyl acetate 80:20), R
f
f
(1d)=0.9, R (3dc)=0.1,
31P NMR (CDCl
calculated for [C27
41.1976.
, 162 MHz): δ=27.88 ppm. HR-MS (ESI+) m/z
-1
3
UV detection]. IR (MIR-ATR, 4000–600 cm ): max=3393, 2955,
+
+
-1 1
H31NaO
2
P] =[M+Na] : 441.1954; found
1605, 1489, 1258, 1183, 976, 811, 736 cm . H NMR (CDCl , 400
3
MHz): δ=7.36 (d, J = 2.0 Hz, 1H, Ar–H), 7.33 (d, J = 2.0 Hz, 1H,
Ar–H), 7.29 (d, J = 2.0 Hz, 1H, Ar–H), 7.26 (d, J = 2.0 Hz, 1H, Ar–
H), 7.16–7.02 (m, 4H, Ar–H), 6.71 (dd, J = 8.8 and 2.0 Hz, 1H,
4
bis(3,5-dimethylphenyl)(5-ethyl-3-methyl-2,3-dihydro-1-
benzofuran-3-yl)phosphine oxide (3cc): GP was carried out
with 4-ethyl-2-iodo-1-[(2-methylprop-2-enyl)oxy]benzene 1c (75.5
mg, 0.25 mmol), bis(3,5-dimethylphenyl)phosphine oxide 2c (64.5
Ar–H), 4.65 (d, J = 9.3 Hz, 1H, OCH
A
B
H ), 4.19 (d, J = 9.3 Hz, 1H,
OCH H ), 2.80–2.55 (m, 2H, CH ), 2.33 (s, 6H, 2 × CH ), 2.29 (s,
6H, 2 × CH ), 1.46 (s, 3H, CH ), 1.24 (s, 9H, 3 × CH ) ppm. 13C
A
B
2
3
3
3
3
mg, 0.25 mmol), Pd
2
(dba)
3
(11.4 mg, 5 mol%), K
2
CO
3
(103.9 mg,
NMR (CDCl , 100 MHz): δ=156.5, 143.7, 138.3 (d, J = 6.6 Hz),
3
0.75 mmol) DMF (0.5 mL), under microwave irradiation (120 C,
138.2 (d, J = 6.6 Hz), 135.5 (d, J = 11.7 Hz), 134.6 (d, J = 96.8
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