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
[61]   MODEL FOR THE INITIAL-STAGE IN THE OXIDATIVE ADDITION OF I2 TO ORGANOPLATINUM(II) COMPOUNDS - X-RAY STRUCTURE OF SQUARE-PYRAMIDAL [PTIII[C6H3(CH2NME2)2-O,O'](ETA-1-I2)] CONTAINING A LINEAR PT-I-I ARRANGEMENT [J].
VANBEEK, JAM ;
VANKOTEN, G ;
SMEETS, WJJ ;
SPEK, AL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (16) :5010-5011
[62]   OXIDATIVE-ADDITION-REDUCTIVE-ELIMINATION REACTIONS OF MONO(ARYL)PLATINUM)II AND BIS(ARYL)PLATINUM(II) COMPLEXES WITH 2 AMINO LIGANDS IN FIXED TRANS POSITIONS - X-RAY CRYSTAL-STRUCTURES OF (2,6-BIS[(DIMETHYLAMINO)METHYL]PHENYL)(4-TOLYL)PLATINUM(IV) DIIODIDE AND (2,6-BIS[(DIMETHYLAMINO)METHYL]PHENYL)PLATINUM(IV) TRICHLORIDE [J].
VANKOTEN, G ;
TERHEIJDEN, J ;
VANBEEK, JAM ;
WEHMANOOYEVAAR, ICM ;
MULLER, F ;
STAM, CH .
ORGANOMETALLICS, 1990, 9 (04) :903-912
[63]  
VEDERNIKOV AN, 1993, ZH ORG KHIM+, V29, P2129
[64]   Lead structures for applications in photodynamic therapy.: Part 1:: Synthesis and variation of m-THPC (Temoporfin) related amphiphilic A2BC-type porphyrins [J].
Wiehe, A ;
Shaker, YM ;
Brandt, JC ;
Mebs, S ;
Senge, MO .
TETRAHEDRON, 2005, 61 (23) :5535-5564
[65]  
Wytko J, 1998, HELV CHIM ACTA, V81, P1964, DOI 10.1002/(SICI)1522-2675(19981111)81:11<1964::AID-HLCA1964>3.0.CO
[66]  
2-I
[67]   Iodine oxidative addition to isomeric platinum(II) phosphine complexes [J].
Yahav, A ;
Goldberg, I ;
Vigalok, A .
ORGANOMETALLICS, 2005, 24 (23) :5654-5659
[68]  
YAHIOGLU G, 2004, Patent No. 2004046151
[69]   Investigation of two rational routes for preparing p-phenylene-linked porphyrin trimers [J].
Yu, LH ;
Lindsey, JS .
TETRAHEDRON, 2001, 57 (45) :9285-9298