Synthesis of brominated directly fused diporphyrins through gold(III)-mediated oxidation

被引:86
作者
Sahoo, Akhila K.
Nakamura, Yasuyuki
Aratani, Naoki
Kim, Kil Suk
Noh, Su Bum
Shinokubo, Hiroshi [1 ]
Kim, Dongho
Osuka, Atsuhiro
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
[2] Kyoto Univ, CREST, Japan Sci & Technol Agcy JST, Kyoto 6068502, Japan
[3] Kyoto Univ, IIC, Kyoto 6068502, Japan
[4] Yonsei Univ, Dept Chem, Seoul 120749, South Korea
[5] Yonsei Univ, Ctr Ultrafast Opt Characterist Control, Seoul 120749, South Korea
关键词
D O I
10.1021/ol061763f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Highly efficient synthesis of meso, meso-dibromo doubly and triply fused diporphyrins has been achieved through a powerful oxidative coupling mediated by AuCl3-AgOTf combination. In addition, palladium-catalyzed debromination of meso-bromoporphyrins has been developed. This debromination protocol enables employment of bromine as a protecting group for the reactive meso-position of porphyrins.
引用
收藏
页码:4141 / 4144
页数:4
相关论文
共 34 条
[1]   Relationship between two-photon absorption and the π-conjugation pathway in porphyrin arrays through dihedral angle control [J].
Ahn, TK ;
Kim, KS ;
Kim, DY ;
Noh, SB ;
Aratani, N ;
Ikeda, C ;
Osuka, A ;
Kim, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1700-1704
[2]   Gold-catalyzed reactions of 2-alkynyl-phenylamines with α,β-enones [J].
Alfonsi, M ;
Arcadi, A ;
Aschi, M ;
Bianchi, G ;
Marinelli, F .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) :2265-2273
[3]   Fusion and planarization of a quinoidal porphyrin dimer [J].
Blake, IM ;
Krivokapic, A ;
Katterle, M ;
Anderson, HL .
CHEMICAL COMMUNICATIONS, 2002, (16) :1662-1663
[4]   Supramolecular patterned surfaces driven by cooperative assembly of C60 and porphyrins on metal substrates [J].
Bonifazi, D ;
Spillmann, H ;
Kiebele, A ;
de Wild, M ;
Seiler, P ;
Cheng, FY ;
Güntherodt, HJ ;
Jung, T ;
Diederich, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (36) :4759-4763
[5]  
CHOU JH, 2000, PORPHYRIN HDB, V6, pCH41
[6]   PALLADIUM-CATALYZED REDUCTIONS OF HALOAROMATIC AND NITROAROMATIC COMPOUNDS WITH TRIETHYLAMMONIUM FORMATE [J].
CORTESE, NA ;
HECK, RF .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (22) :3491-3494
[7]   meso-alkyl-substituted meso-meso linked diporphyrins and meso-alkyl-substituted meso-meso, β-β, β-β triply linked diporphyrins [J].
Hiroto, S ;
Osuka, A .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :4054-4058
[8]   Synthesis and characterization of facially encumbered and soluble porphyrin tapes [J].
Ikeda, Toshiaki ;
Tsuda, Akihiko ;
Aratani, Naoki ;
Osuka, Atsuhiro .
CHEMISTRY LETTERS, 2006, 35 (08) :946-947
[9]   Synthesis of doubly strapped meso-meso-linked porphyrin arrays and triply linked conjugated porphyrin tapes [J].
Ikeda, Toshiaki ;
Lintuluoto, Juha M. ;
Aratani, Naoki ;
Yoon, Zin Seok ;
Kim, Dongho ;
Osuka, Atsuhiro .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (14) :3193-3204
[10]   Synthesis and characterization of fully conjugated porphyrin tapes [J].
Ikeue, T ;
Aratani, N ;
Osuka, A .
ISRAEL JOURNAL OF CHEMISTRY, 2005, 45 (03) :293-302