K. Suzuki et al. / Tetrahedron Letters 47 (2006) 5789–5792
5791
11. Selected examples of Pd-catalyzed reactions with ( )-
BINAP derivatives as ligand: (a) Wolf, J. P.; Wagaw, S.;
Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215; (b)
Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119,
11108; (c) Kuwabe, S.; Torraca, K. E.; Buchwald, S. L.
J. Am. Chem. Soc. 2001, 123, 12202, and references cited
therein.
13C NMR (CDCl3): d = 55.26, 73.19, 113.87, 123.86,
124.08, 125.22, 125.43, 125.95, 128.21, 128.30, 128.63,
130.47, 133.76, 135.30, 138.81, 158.92. EIMS: m/z = 264
(M+), 247, 135, 77. HRMS (M+) calcd for C18H16O2:
264.1150, found 264.1154. Anal. calcd for C18H16O2: C,
81.79; H, 6.10. Found C, 81.49; H, 6.18.
1-Naphthyl-(2-tolyl)methanol (entry 5). IR (Nujol):
12. Representative procedure for the Pd-catalyzed arylation of
1-naphthaldehyde (1) with phenylboronic acid: To a stirred
solution of Pd(OAc)2 (5.6 mg, 0.025 mmol) in DME/H2O
(5:1, 2.4 mL) were added ( )-tol-BINAP (17.0 mg,
0.025 mmol), NaOt-Bu (96.1 mg, 1.0 mmol), PhB(OH)2
(122 mg, 1.0 mmol), and 1-naphthaldehyde (1) (76.1 mg,
0.5 mmol) at rt. The reaction mixture was stirred at 100 ꢁC
for 24 h under argon atmosphere, allowed to cool, diluted
with H2O and extracted with EtOAc. The combined
extracts were washed with brine, dried (Na2SO4) and
concentrated. The residue was purified by silica gel column
(EtOAc/hexane = 1:19 to 1:9) to give (1-naphthyl)phenyl-
methanol (2) (101 mg, yield 86%) as a colorless oil. The
physical data as shown below were comparable to those
m = 3218 cmꢀ1 1H NMR (CDCl3): d = 2.19 (br d,
.
J = 3.9 Hz, 1H), 2.30 (s, 3H), 6.64–6.76 (d, J = 3.9 Hz,
1H), 7.10–7.28 (m, 3H), 7.31–7.54 (m, 5H), 7.76–7.92 (m,
2H), 8.00–8.08 (m, 1H). 13C NMR (CDCl3): d = 19.26,
69.95, 123.45, 124.48, 125.24, 125.55, 126.05, 126.25,
126.60, 127.59, 128.39, 128.69, 130.42, 131.01, 133.75,
135.66, 138.10, 140.77. FABMS: m/z = 249 (M++1).
Anal. calcd for C18H16O: C, 87.06; H, 6.49. Found C,
87.31; H, 6.59.
2-Naphthylphenylmethanol (entry 6). The physical data as
shown below were comparable to those reported: Seebach,
D.; Beck, A. K.; Roggo, S.; Wonnacotto, A. Chem. Ber.
1985, 118, 3673. IR (Nujol): m = 3227 cmꢀ1 1H NMR
.
(CDCl3): d = 2.34 (br s, 1H), 6.02 (s, 1H), 7.24–7.54 (m,
8H), 7.76–7.89 (m, 3H), 7.91 (s, 1H). 13C NMR (CDCl3):
d = 76.33, 124.64, 124.87, 125.86, 126.08, 126.58, 127.56,
127.94, 128.22, 128.43, 132.71, 133.08, 140.93, 143.45.
EIMS: m/z = 234 (M+), 155, 129, 105, 77. Anal. calcd
for C17H14O: C, 87.15; H, 6.02. Found C, 87.27; H,
6.38.
1
reported.2a IR (neat): m = 3381 cmꢀ1. H NMR (CDCl3):
d = 2.42 (s, 1H), 6.48 (s, 1H), 7.21–7.48 (m, 8H), 7.59 (d,
J = 7.1 Hz, 1H), 7.74–7.86 (m, 2H), 7.98–8.02 (m, 1H).
13C NMR (CDCl3): d = 73.50, 123.86, 124.48, 125.17,
125.44, 125.98, 126.90, 127.48, 128.29, 128.35, 128.60,
130.54, 133.75, 138.63, 142.94. EIMS: m/z = 234 (M+),
217, 157, 129, 128, 105, 77. Anal. calcd for C17H14O: C,
87.15; H, 6.02. Found C, 86.95; H, 5.99.
4-Fluorophenylphenylmethanol (entry 7). The spectral data
as shown below were comparable to those reported:
Wang, Z.; Chandler, W. D.; Lee, D. G. Can. J. Chem.
The physical data of other diarylmethanols are shown
below.
.
1998, 76, 919. IR (neat): m = 3354 cmꢀ1 1H NMR
4-Fluorophenyl-1-naphthylmethanol (Table 3, entry 1). IR
(CDCl3): d = 2.19 (br d, J = 3.3 Hz, 1H), 5.83 (br d,
J = 3.3 Hz, 1H), 6.99 (d, J = 8.7 Hz, 1H), 7.03 (d,
J = 8.7 Hz, 1H), 7.22–7.40 (m, 7H). 13C NMR (CDCl3):
d = 75.63 (br), 115.22 (d, J = 21.0 Hz), 126.38, 127.65,
128.14 (d, J = 8.0 Hz), 128.49, 139.46 (d, J = 3.0 Hz),
143.55, 162.04 (d, J = 245 Hz). EIMS: m/z = 202 (M+),
183, 105, 77. Anal. calcd for C13H11FO: C, 77.21; H, 5.48.
Found C, 77.39; H, 5.70.
(neat): m = 3236 cmꢀ1 1H NMR (CDCl3): d = 2.25–2.40
.
(br, 1H), 6.52 (br s, 1H), 6.99 (d, J = 8.7 Hz, 1H), 7.02 (d,
J = 8.7 Hz, 1H), 7.29–7.53 (m, 5H), 7.63 (d, J = 6.8 Hz,
1H), 7.79–7.91 (m, 2H), 7.95–8.02 (m, 1H). 13C NMR
(CDCl3): d = 73.03, 115.24 (d, J = 21.2 Hz), 123.73,
124.42, 125.21, 125.58, 126.11, 128.53, 128.62 (d,
J = 8.4 Hz), 128.72, 130.40, 133.83, 138.44, 138.70 (d,
J = 3.4 Hz), 162.00 (d, J = 245.4 Hz). FABMS: m/z = 253
(M++1). Anal. calcd for C17H13FO: C, 80.93; H, 5.19.
Found C, 81.11; H, 5.43.
4-Chlorophenylphenylmethanol (entry 8). The spectral
data as shown below were comparable to those reported:
Chen, D.-W.; Ochiai, M. J. Org. Chem. 1999, 64, 6804. IR
4-Chlorophenyl-1-naphthylmethanol (entry 2). IR (Nujol):
m = 3295 cmꢀ1. 1H NMR (CDCl3): d = 2.31–2.42 (br, 1H),
6.49 (br s, 1H), 7.28 (d, J = 8.6 Hz, 2H), 7.34 (d,
J = 8.6 Hz, 2H), 7.38–7.52 (m, 3H), 7.58 (d, J = 6.8 Hz,
1H), 7.74–7.92 (m, 2H), 7.94–8.03 (m, 1H). 13C NMR
(CDCl3): d = 72.84, 123.66, 124.56, 125.13, 125.58, 126.12,
128.18, 128.41, 128.55, 128.66, 130.32, 133.10, 133.72,
138.10, 141.25. EIMS: m/z = 270 (M+), 268 (M+), 253,
251, 129, 128, 77. HRMS (M+) calcd for C17H13Cl37O
270.0625, found 270.0631. HRMS (M+) calcd for
C17H13Cl35O 268.0654, found 268.0659. Anal. calcd for
C17H13ClO: C, 75.98; H, 4.88. Found C, 76.10; H, 5.23.
1-Naphthyl-(4-tolyl)methanol (entry 3). IR (Nujol): m =
3353 cmꢀ1. 1H NMR (CDCl3): d = 2.28 (s, 3H), 2.55 (br s,
1H), 6.40 (br s, 1H), 7.07 (d, J = 7.9 Hz, 1 · 2H), 7.22 (d,
J = 7.9 Hz, 1 · 2H), 7.34–7.48 (m, 3H), 7.59 (d,
J = 6.9 Hz, 1H), 7.73–7.90 (m, 2H), 7.94–8.05 (m, 1H).
13C NMR (CDCl3): d = 21.18, 73.38, 123.86, 124.23,
125.19, 125.40, 125.93, 126.90, 128.18, 128.59, 129.07,
130.50, 133.73, 137.20, 138.75, 140.06. FABMS: m/z =
249 (M++1). Anal. calcd for C18H16O: C, 87.06; H, 6.49.
Found C, 87.10; H, 6.44.
(neat): m = 3341 cmꢀ1 1H NMR (CDCl3): d = 2.34 (d,
.
J = 3.6 Hz, 1H), 6.23 (d, J = 3.6 Hz, 1H), 7.18–7.45 (m,
8H), 7.61 (dd, J = 7.7, 1.7 Hz, 1H). 13C NMR (CDCl3):
d = 72.55, 126.78, 126.93, 127.61, 127.81, 128.31, 128.57,
129.35, 132.27, 140.74, 141.98. FABMS: m/z = 221
(M++1), 219 (M++1). Anal. calcd for C13H11ClO: C,
71.40; H, 5.07. Found C, 71.36; H, 5.05.
Phenyl-(4-tolyl)methanol (entry 9). The spectral data as
shown below were comparable to those reported: Seebach,
D.; Beck, A. K.; Roggo, S.; Wonnacotto, A. Chem. Ber.
1985, 118, 3673. IR (Nujol): m = 3330 cmꢀ1 1H NMR
.
(CDCl3): d = 2.14 (br d, J = 3.3 Hz, 1H), 2.33 (s, 3H),
5.82 (br d, J = 3.3 Hz, 1H), 7.14 (d, J = 7.9 Hz, 1H · 2),
7.26 (d, J = 7.9 Hz, 1H · 2), 7.28–7.42 (m, 5H). 13C NMR
(CDCl3): d = 21.16, 76.10, 126.35, 126.42, 127.34, 128.32,
129.06, 137.15, 140.85, 143.84. EIMS: m/z = 198 (M+),
183, 105, 77. Anal. calcd for C14H14O: C, 84.81; H, 7.12.
Found C, 84.69; H, 6.86.
2-Methoxyphenylphenylmethanol (entry 10). The physical
data as shown below were comparable to those reported:
Oi, S.; Moro, M.; Inoue, Y. Organometallics 2001, 20,
.
1036. IR (neat): m = 3403 cmꢀ1 1H NMR (CDCl3):
4-Methoxyphenyl-1-naphthylmethanol (entry 4). IR
d = 3.04 (d, J = 5.4 Hz, 1H), 3.82 (s, 3H), 6.06 (d,
J = 5.4 Hz, 1H), 6.90 (d, J = 8.5 Hz, 1H), 6.94 (dd,
J = 7.6, 7.6 Hz, 1H), 7.19–7.43 (m, 7H). 13C NMR
(CDCl3): d = 55.32, 72.06, 110.54, 120.61, 126.37,
126.96, 127.62, 127.98, 128.52, 131.72, 143.04. EIMS:
(Nujol): m = 3536 cmꢀ1 1H NMR (CDCl3): d = 2.43 (br
.
s, 1H), 3.73 (s, 3H), 6.43 (s, 1H), 6.81 (d, J = 8.7 Hz, 2H),
7.26 (d, J = 8.7 Hz, 2H), 7.36–7.49 (m, 3H), 7.64 (d,
J = 7.1 Hz, 1H), 7.74–7.87 (m, 2H), 7.90–7.99 (m, 1H).