Efficient microwave-assisted synthesis of amine-substituted tetrakis (pentafluorophenyl) porphyrin

被引：79

作者：

Samaroo, Diana

Soll, Clifford E.

Todaro, Louis J.

Drain, Charles M.

机构：

[1] CUNY Hunter Coll, Dept Chem & Biochem, New York, NY 10021 USA

[2] CUNY Hunter Coll, Grad Ctr, New York, NY 10021 USA

[3] Rockefeller Univ, New York, NY 10021 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 22期

关键词：

D O I：

10.1021/ol060946z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report an efficient and rapid means for the synthesis of tetrakis(pentafluorophenyl) porphyrin (TPPF20) derivatives by microwave irradiation in an environmentally acceptable solvent. The selective displacement of the para-fluorine groups in TPPF20 by primary amines occurs in yields between 70 and 95%. This method demonstrates that TPPF20 is an ideal platform for the rapid formation of porphyrin conjugates for therapeutic, catalytic, and other applications.

引用

页码：4985 / 4988

页数：4

共 18 条

[1] PREPARATION OF FUNCTIONALIZED POLYHALOGENATED TETRAARYL-PORPHYRINS BY SELECTIVE SUBSTITUTION OF THE PARA-FLUORINES OF MESO-TETRA-(PENTAFLUOROPHENYL)PORPHYRINS
BATTIONI, P
BRIGAUD, O
DESVAUX, H
MANSUY, D
TRAYLOR, TG
[J]. TETRAHEDRON LETTERS, 1991, 32 (25) : 2893 - 2896
[2] Poly(ethylene glycol)-supported tetrahydroxyphenyl porphyrin: A convenient, recyclable catalyst for photooxidation reactions
Benaglia, M
Danelli, T
Fabris, F
Sperandio, D
Pozzi, G
[J]. ORGANIC LETTERS, 2002, 4 (24) : 4229 - 4232
[3] Efficient microwave-assisted synthesis of new sulfonylbenzimidazole-4,7-diones: heterocyclic quinones with potential antitumor activity
Boufatah, N
Gellis, A
Maldonado, J
Vanelle, P
[J]. TETRAHEDRON, 2004, 60 (41) : 9131 - 9137
[4] Chaouchi M, 2002, EUR J ORG CHEM, V2002, P1278
[5] Efficient synthesis and photodynamic activity of porphyrin-saccharide conjugates: Targeting and incapacitating cancer cells
Chen, X
Hui, L
Foster, DA
Drain, CM
[J]. BIOCHEMISTRY, 2004, 43 (34) : 10918 - 10929
[6] A perspective on four new porphyrin-based functional materials and devices
Drain, CM
Hupp, JT
Suslick, KS
Wasielewski, MR
Chen, X
[J]. JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2002, 6 (04) : 243 - 258
[7] Synthesis of meso substituted porphyrins in air without solvents or catalysts
Drain, CM
Gong, XC
[J]. CHEMICAL COMMUNICATIONS, 1997, (21) : 2117 - 2118
[8] Hamblin MR, 2001, CANCER RES, V61, P7155
[9] Microwave-assisted synthesis of phthalocyanine-porphyrin complex and its photoelectric conversion properties
Liu, MO
Hu, AT
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (15) : 2450 - 2455
[10] Microwave-assisted synthesis and reverse saturable absorption of phthalocyanines and porphyrins
Liu, MO
Tai, CH
Wang, WY
Chen, JR
Hu, AT
Wei, TH
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (06) : 1078 - 1084

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