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A Facile and Potent Synthesis of meso , meso ‐Linked Porphyrin Arrays Using Iodine( III ) Reagents
Author(s) -
Jin LiMei,
Chen Liang,
Yin JuanJuan,
Guo CanCheng,
Chen QingYun
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500255
Subject(s) - chemistry , reagent , substituent , iodine , porphyrin , benzene , combinatorial chemistry , medicinal chemistry , organic chemistry
The synthesis of meso , meso ‐linked fluoroalkylporphyrin arrays has been accomplished, in excellent yields, by the simple treatment of a CHCl 3 solution of zincated 5‐fluoroalkyl‐10,20‐diarylporphyrins (where fluoroalkyl = CF 3 , ClC 2 F 4 , n ‐ClC 4 F 8 , n ‐C 6 F 13 , etc.) with iodine( III ) reagents such as PhI(O–CO–CF 3 ) 2 (PIFA, also named as bis(trifluoroacetoxy)iodo]benzene) or PhI(OAc) 2 (PIDA). For nonfluorinated zincated 5‐substituted‐10–20‐diarylporphyrins (where substituent = phenyl, 4‐methoxyphenyl, 4‐methylphenyl, etc.) the similar coupling reactions also proceed fast and quantitatively. Moreover, various 15‐unsubstituted metalloporphyrins can also be coupled in high yields. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)