meso-iodo- and meso-iodovinylporphyrins via organo-palladium porphyrins and the crystal structure of 5-iodo-10,20-diphenylporphyrin

被引:28
作者
Atefi, Farzad
Locos, Oliver B.
Senge, Mathias O.
Arnold, Dennis P.
机构
[1] Queensland Univ Technol, Sch Phys & Chem Sci, Synth & Mol Recognit Program, Brisbane, Qld 4001, Australia
[2] Univ Dublin Trinity Coll, SFI Tetrapyrrole Lab, Sch Chem, Dublin 2, Ireland
关键词
porphyrinoids; iodination; palladium; organometallic; crystal structure;
D O I
10.1142/S1088424606000211
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The regiospecific halogen exchange reactions of various easily accessible mesobromoporphyrins to obtain meso-iodoporphyrins, using eta(1)-palladioporphyrins as intermediates, have been investigated. This one-pot methodology allows the isolation of meso-iodoporphyrins in excellent yields with short reaction times. Similarly nieso-(2-bromoethenyl)porphyrins can be converted to their iodoethenyl analogues. These iodoporphyrins show great potential as starting materials for various palladium catalyzed reactions. The X-ray crystal structure of 5-iodo-10,20-diphenylporphyrin has been determined. Copyright (c) 2006 Society of Porphyrins & Phthalocyanines.
引用
收藏
页码:176 / 185
页数:10
相关论文
共 69 条
[1]  
[Anonymous], 1972, Inorg. Synth, DOI DOI 10.1002/9780470132449.CH23
[2]  
[Anonymous], 1996, PALLADIUM REAGENTS C
[3]   meso-η1-metalloporphyrins:: preparation of palladio- and platinioporphyrins and the crystal structure of 5-[bromo-1,2-bis(diphenylphosphino)ethanepalladio(II)-10,20-diphenylporphyrin [J].
Arnold, DP ;
Sakata, Y ;
Sugiura, K ;
Worthington, EI .
CHEMICAL COMMUNICATIONS, 1998, (21) :2331-2332
[4]   Butadiyne-linked bis(chlorin) and chlorin-porphyrin dyads and an improved synthesis of bis[octaethylporphyrinatonickel(II)-5-yl]butadiyne using the Takai iodoalkenation [J].
Arnold, DP ;
Hartnell, RD .
TETRAHEDRON, 2001, 57 (07) :1335-1345
[5]   SOME REACTIONS OF MESO-FORMYLOCTAETHYLPORPHYRIN [J].
ARNOLD, DP ;
JOHNSON, AW ;
MAHENDRAN, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (04) :366-370
[6]   Functionalization of 5,15-diphenylporphyrin: Preparation and X-ray crystal structures of meso nitro, bromo, and trimethylsilylethynyl derivatives [J].
Arnold, DP ;
Bott, RC ;
Eldridge, H ;
Elms, FM ;
Smith, G ;
Zojaji, M .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1997, 50 (05) :495-503
[7]   Peripherally-metallated porphyrins:: synthesis and spectra of meso-η1-palladio- and platinioporphyrins and the crystal structures of cis-{PtBr[l 0,20-diphenylporphyrinatonickel(II)-5-yl](PPh3)2} and trans-{PtBr[10,20-diphenylporphyrin-5-yl](PPh3)2}•0.25CH2Cl2 [J].
Arnold, DP ;
Healy, PC ;
Hodgson, MJ ;
Williams, ML .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 607 (1-2) :41-50
[8]  
ATEFI F, 2006, UNPUB
[9]   2-aminopyrimidine directed self-assembly of zinc porphyrins containing bulky 3,5-di-tert-butylphenyl groups [J].
Balaban, TS ;
Goddard, R ;
Linke-Schaetzel, M ;
Lehn, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (14) :4233-4239
[10]   Preparation of novel highly conjugated bis-porphyrin bridged with a polyene linker [J].
Blart, E ;
Suzenet, F ;
Quintard, JP ;
Odobel, F .
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2003, 7 (4-5) :207-213