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General Procedure
for the Synthesis of Naphthalene Derivatives 6 by One-Pot Reaction
A
mixture of N-(diphenylmethylene)aniline
(1, 129 mg, 0.500 mmol), 4-bromobenzaldehyde
(2a, 1.00 mmol) or 4-iodobenzaldehyde (2b, 1.00 mmol), olefin (4,
0.600 mmol), 4 Å MS (200 mg), [ReBr(CO)3(thf)]2 (10.6
mg, 0.0125 mmol), and toluene (1.0 mL) was stirred at 115 ˚C
for 48 h. Then, AcOH (3.0 mL) and H2SO4 (1.0
mL) were added, and the mixture was stirred at r.t. for 2 h. The
crude product was extracted with hexane and purified by column chromatography
on silica gel or recrystallized from EtOH to give naphthalene derivative 6.
<A NAME="RU05111ST-14">14</A>
Typical Procedure
for the Synthesis of
meso
-Substituted Tetraarylalkynylporphyrin 9a
Porphyrins 7
¹¹ and 8
¹²a were
prepared according to the reported methods. To a degassed solution
of zinc(II) 5,10,15,20-tetraethynylporphyrin (8,
10 mg, 0.021 mmol), 1-(4-iodophenyl)-4-phenylnaphthalene-2,3-dicarboxylic acid
diethyl ester (6d, 75.4 mg, 0.137 mmol),
and AsPh3 (12 mg, 0.038 mmol) in a mixture of anhyd THF
(10 mL) and Et3N (5.0 mL) was added Pd2(dba)3 (2.0
mg, 0.0020 mmol). The reaction mixture was stirred at 50 ˚C
for 4 h under an argon atmosphere. The solvent was evaporated under reduced
pressure, and the crude product was purified by column chromatography
on silica gel using CHCl3 as an eluent to give a dark
green solid 9a (41.7 mg, 92%). ¹H
NMR (400 MHz, CDCl3): δ = 0.96 (t, J = 7.2 Hz,
12 H), 1.17 (t, J = 7.2
Hz, 12 H), 4.03 (q, J = 7.2
Hz, 8 H), 4.19 (q, J = 7.2 Hz,
8 H), 7.43-7.55 (m, 28 H), 7.68-7.71 (m, 12 H),
7.85 (d, J = 8.4
Hz, 4 H), 8.27 (d, J = 8.0
Hz, 8 H), 9.48 (s, 8 H). ¹³C NMR (100
MHz, CDCl3): δ = 13.6, 13.9, 61.4,
61.6, 66.7, 92.8, 96.9, 102.7, 123.7, 127.1, 127.5, 127.8, 127.9,
128.1, 129.0, 129.2, 130.2, 130.7, 131.2, 131.5, 132.6, 132.8, 137.7,
138.3, 138.4, 139.3, 151.3, 168.3, 168.4. IR (Nujol): 480, 771,
941, 1132, 1166, 1222, 1300, 1676, 1685, 1716, 1734, 2213, 2924
cm-¹.