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Synlett 2011(15): 2177-2180  
DOI: 10.1055/s-0030-1261199
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of meso-Substituted Tetraarylalkynylporphyrins via Rhenium-Catalyzed Formation of Naphthalene Units

Ali Samarata, Yoichiro Kuninobu*b, Kazuhiko Takai*b
a University of Carthage, Faculty of Sciences of Bizerte, Jarzouna 7021, Bizerte, Tunisia
b Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Kita-ku, Okayama 700-8530, Japan
Fax: +81(86)2518094; e-Mail: kuninobu@cc.okayama-u.ac.jp; e-Mail: ktakai@cc.okayama-u.ac.jp;
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Publication History

Received 11 July 2011
Publication Date:
30 August 2011 (online)

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Abstract

Rhenium-catalyzed synthesis of naphthalene-substituted aryl bromides or iodides via C-H bond activation, and its use for palladium-catalyzed cross-coupling reactions with tetraethynylporphyrin are described. A series of novel meso-substituted tetraalkynylporphyrins with naphthalene moieties were obtained.

Key words

rhenium catalyst - C-H bond activation - naphthalene derivative - Sonogashira coupling - meso-substituted tetraalkynyl­porphyrin

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13

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.

14

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.