4
G. Hamasaka et al. / Tetrahedron xxx (2015) 1e5
3-(4-methoxyphenyl)prop-2-en-1-yl acetate (2c),8 (2E)-3-(4-
methylphenyl)prop-2-en-1-yl acetate (2E)-3-[4-(tri-
(2d),8
(100 MHz, CDCl3) d 158.8, 140.4, 130.4, 130.3, 128.6, 128.4, 127.2,
127.0, 126.1, 113.9, 55.3, 39.3; EIMS m/z 224 [Mþ].
fluoromethyl)phenyl]prop-2-en-1-yl acetate (2e),8 (2E)-3-(2-
methoxyphenyl)prop-2-en-1-yl acetate (2f),8 (2E)-3-(2-naphthyl)
prop-2-en-1-yl acetate (2g),9 (2E)-3-(2-thienyl)prop-2-en-1-yl ac-
etate (2h),8 cyclohex-2-en-1-yl acetate (2j),10 sodium tetrakis(4-
methylphenyl)borate (3b),11 and sodium tetrakis(4-fluorophenyl)
borate (3c)11 were prepared by the reported methods.
4.4.4. 1-Methyl-4-[(1E)-3-phenylprop-1-en-1-yl]benzene (4da). [-
CAS: 134539-87-0].7d 1H NMR (396 MHz, CDCl3)
d 7.35e7.19 (m, 7H,
ArH), 7.10 (d, J¼8.3 Hz, 2H, ArH), 6.43 (d, J¼15.4 Hz, 1H, eCH]
CHCH2e), 6.30 (dt, J¼15.4, 7.0 Hz, 1H, eCH]CHCH2e), 3.54 (d,
J¼7.0 Hz, 2H, eCH]CHCH2e), 2.31 (s, 3H, CH3); 13C NMR (100 MHz,
CDCl3)
d 140.3, 136.8, 134.7, 130.9, 129.2, 128.7, 128.4, 128.1, 126.1,
4.2. Preparation of 1avscl
126.0, 39.3, 21.2; EIMS m/z 208 [Mþ].
A chloroform solution of 1a (0.1 mL, 10 mg/mL) was charged in
a 4 mL vial equipped with a screw cap. After evaporation of the
chloroform, a thin film of 1a was formed on the inner glass surface
of the vial. Then, 1 mL of Millipore water was added to the vial
followed by heating the resulting mixture at 80 ꢀC for 12 h without
stirring. After standing at 25 ꢀC for overnight, the resulting mixture
was sonicated for 10 min to generate a yellow suspension of vesi-
4.4.5. 1-[(1E)-3-Phenylprop-1-en-1-yl]-4-(trifluoromethyl)-benzene
(4ea). [CAS: 62056-35-3].12 1H NMR (396 MHz, CDCl3)
d 7.53 (d,
J¼8.0 Hz, 2H, ArH), 7.43 (d, J¼8.0 Hz, 2H, ArH), 7.35e7.23 (m, 5H,
ArH), 6.48e6.46 (m, 2H, eCH]CHCH2e), 3.57 (d, J¼3.7 Hz, 2H,
eCH]CHCH2e); 13C NMR (100 MHz, CDCl3)
d 140.9, 139.6, 132.1,
129.8, 128.9 (q, J¼32.4 Hz), 128.7, 128.6, 126.4, 126.3, 125.5 (q,
J¼3.8 Hz), 124.3 (q, J¼271.8 Hz), 39.4; EIMS m/z 262 [Mþ].
cles 1avscl
.
4.4.6. 1-Methoxy-2-[(1E)-3-phenylprop-1-en-1-yl]benzene (4fa). [-
CAS: 1246889-00-6].13 1H NMR (396 MHz, CDCl3) d 7.6 0 (d,
J¼7.5 Hz, 1H, ArH), 7.46e7.41 (m, 2H, ArH), 7.37e7.16 (m, 4H, ArH),
6.92e6.85 (m, 2H, ArH), 6.82 (d, J¼15.8 Hz, 1H, eCH]CHCH2e),
6.42 (dt, J¼15.8, 7.1 Hz, 1H, eCH]CHCH2e), 3.85 (s, 3H, eOCH3),
3.57 (d, J¼7.1 Hz, 2H, eCH]CHCH2e); 13C NMR (100 MHz, CDCl3)
d 156.4, 140.5, 129.7, 128.6, 128.4, 128.1, 126.5, 126.4, 126.0, 125.7,
120.5, 110.7, 55.3, 39.8; EIMS m/z 224 [Mþ].
4.3. Preparation of 1bvscl
A chloroform solution of 1b (0.1 mL, 10 mg/mL) was charged in
a 4 mL vial equipped with a screw cap. After evaporation of the
chloroform, a thin film of 1b was formed on the inner glass surface
of the vial. Then, 1 mL of Millipore water was added to the vial
followed by heating the resulting mixture at 60 ꢀC for 4 h without
stirring. After standing at 25 ꢀC for overnight, the resulting mixture
was sonicated for 10 min to generate a yellow suspension of vesi-
4.4.7. 2-[(1E)-3-Phenylprop-1-en-1-yl]naphthalene
(4ga). [CAS:
cles 1bvscl
.
5751-32-6].14 1H NMR (396 MHz, CDCl3)
d
7.79e7.74 (m, 3H, ArH),
7.70 (s, 1H, ArH), 7.58 (dd, J¼8.3, 1.8 Hz, 1H, ArH), 7.46e7.39 (m, 2H,
ArH), 7.29e7.22 (m, 5H, ArH), 6.62 (d, J¼15.7 Hz, 1H, eCH]
CHCH2e), 6.49 (dt, J¼15.7, 6.9 Hz, 1H, eCH]CHCH2e), 3.61 (d,
4.4. Allylic arylation in water; typical procedure
A vial equipped with a screw cap was charged with a suspension
of 1avscl (1.0 mg, 8.5ꢁ10ꢂ4 mmol), NaBPh4 (3a) (23.3 mg,
0.068 mmol), and (2E)-3-biphenyl-4-ylprop-2-en-1-yl acetate (2a)
(8.6 mg, 0.034 mmol) in H2O (1 mL). The mixture was agitated by
shaking at 50 ꢀC for 10 min then allowed to cool to 25 ꢀC. The cooled
mixture was extracted with t-BuOMe (4ꢁ1.0 mL), and the organic
layers were combined, dried over Na2SO4, and concentrated under
reduced pressure. The residue was purified by chromatography
(silica gel, hexane) to give 4-[(1E)-3-phenylprop-1-en-1-yl]bi-
phenyl (4aa; 5.4 mg, 0.020 mmol, 59%) as a white solid.
J¼6.9 Hz, 2H, eCH]CHCH2e); 13C NMR (100 MHz, CDCl3)
d 140.1,
134.9, 133.6, 132.7, 131.1, 129.6, 128.7, 128.5, 128.1, 127.8, 127.6, 126.2,
126.1, 125.7, 125.5, 123.5, 39.4; EIMS m/z 244 [Mþ].
4.4.8. 2-[(1E)-3-Phenylprop-1-en-1-yl]thiophene
1403462-93-0].15 1H NMR (396 MHz, CDCl3)
(4ha). [CAS:
7.33e7.30 (m, 2H,
d
ArH), 7.26e7.21 (m, 3H, ArH), 7.10 (d, J¼4.8 Hz, 1H, thiophene 5-H),
6.93 (dd, J¼4.8, 3.2 Hz, 1H, thiophene 4-H), 6.89 (d, J¼3.2 Hz, 1H,
thiophene 3-H), 6.56 (d, J¼15.6 Hz, 1H, eCH]CHCH2e), 6.21 (dt,
J¼15.6, 6.7 Hz, 1H, eCH]CHCH2e), 3.51 (d, J¼6.7 Hz, 2H, eCH]
CHCH2e); 13C NMR (100 MHz, CDCl3)
d 142.6, 139.8, 129.1, 128.7,
4.4.1. 4-[(1E)-3-Phenylprop-1-en-1-yl]biphenyl (4aa). White solid;
128.5, 127.2, 126.2, 124.8, 124.2, 123.5, 39.1; EIMS m/z 200 [Mþ].
mp 90e91 ꢀC; 1H NMR (396 MHz, CDCl3)
d 7.60e7.52 (m, 4H, ArH),
7.45e7.41 (m, 4H, ArH), 7.35e7.31 (m, 2H, ArH), 7.27e7.21 (m, 4H,
ArH), 6.50 (d, J¼15.6 Hz, 1H, eCH]CHCH2e), 6.41 (dt, J¼15.6,
6.5 Hz, 1H, eCH]CHCH2e), 3.58 (d, J¼6.5 Hz, 2H, eCH]CHCH2e);
4.4.9. (2E)-Hex-2-en-1-ylbenzene (4ia). [CAS: 78633-31-5].7d 1H
NMR (396 MHz, CDCl3)
d 7.31e7.27 (m, 2H, ArH), 7.20e7.18 (m, 3H,
ArH), 5.57 (dt, J¼15.0, 5.9 Hz, 1H, eCH]CHCH2Ph), 5.50 (dt, J¼15.4,
5.9 Hz, 1H, eCH]CHCH2Ph), 3.33 (d, J¼5.9 Hz, 2H, eCH]
CHCH2Ph), 2.00 (q, J¼6.7 Hz, 2H, eCH2CH]CHCH2Ph), 1.40 (sext,
J¼7.4 Hz, 2H, eCH2CH2CH]CHCH2Ph), 0.90 (t, J¼7.4 Hz, 3H, eCH3);
13C NMR (100 MHz, CDCl3)
d 140.7, 140.1, 139.8, 136.5, 130.6, 129.4,
128.7, 128.7, 128.5, 127.2 (2C), 126.9, 126.5, 126.2, 39.4; IR (ATR):
1600, 1487, 966, 836, 754, 700, 685, 588 cmꢂ1; EIMS m/z 270 [Mþ];
Anal. Calcd for C21H18: C, 93.29: H, 6.71%. Found: C, 93.24: H, 6.71%.
13C NMR (100 MHz, CDCl3)
d 141.1, 131.9, 128.9, 128.4, 128.3, 125.8,
39.1, 34.6, 22.6, 13.7; EIMS m/z 160 [Mþ].
4.4.2. 1,10-(1E)-Prop-1-ene-1,3-diyldibenzene (4ba). [CAS: 3412-44-
0].7d 1H NMR (396 MHz, CDCl3)
d
7.37e7.18 (m, 10H, ArH), 6.46 (d,
4.4.10. 1-(Cyclohex-2-enyl)benzene (4ja). [CAS: 15232-96-9].7d 1H
J¼15.8 Hz, 1H, eCH]CHCH2e), 6.36 (dt, J¼15.8, 6.7 Hz, 1H, eCH]
NMR (396 MHz, CDCl3) d 7.32e7.28 (m, 2H, ArH), 7.23e7.18 (m, 3H,
CHCH2e), 3.55 (d, J¼6.7 Hz, 2H, eCH]CHCH2e); 13C NMR
ArH), 5.91e5.88 (m, 1H, eCH]CHeCHPhe), 5.73e5.70 (m, 1H,
eCH]CHeCHPhe), 3.43e3.38 (m, 1H, eCH]CHeCHPhe),
2.11e1.98 (m, 3H, e(CH2)3eCHPhe), 1.77e1.72 (m, 1H,
e(CH2)3eCHPhe), 1.67e1.51 (m, 2H, e(CH2)3eCHPhe); 13C NMR
(100 MHz, CDCl3) d 140.2, 137.5, 131.1, 129.3, 128.7, 128.5 (2C), 127.2,
126.2, 126.2, 39.4; EIMS m/z 194 [Mþ].
4.4.3. 1-Methoxy-4-[(1E)-3-phenylprop-1-en-1-yl]benzene
(100 MHz, CDCl3) d 140.6, 130.1, 128.3, 128.2, 127.7, 125.9, 41.8, 32.6,
(4ca). [CAS: 35856-81-6].7d 1H NMR (396 MHz, CDCl3)
d
7.33e7.20
25.0, 21.2; EIMS m/z 158 [Mþ].
(m, 7H, ArH), 6.83 (d, J¼8.7 Hz, 2H, ArH), 6.40 (d, J¼15.7 Hz, 1H,
eCH]CHCH2e), 6.22 (dt, J¼15.7, 6.8 Hz, 1H, eCH]CHCH2e), 3.80
(s, 3H, eOCH3), 3.53 (d, J¼6.8 Hz, 2H, eCH]CHCH2e); 13C NMR
4.4.11. 1-Methyl-4-[(2E)-3-phenylprop-2-en-1-yl]benzene
(4bb). [CAS: 134539-86-9].7d 1H NMR (396 MHz, CDCl3)
d 7.35 (d,