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

被引：80

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

收藏

页码：4985 / 4988

页数：4

相关论文

共 18 条

[1] PREPARATION OF FUNCTIONALIZED POLYHALOGENATED TETRAARYL-PORPHYRINS BY SELECTIVE SUBSTITUTION OF THE PARA-FLUORINES OF MESO-TETRA-(PENTAFLUOROPHENYL)PORPHYRINS [J].

BATTIONI, P ;

BRIGAUD, O ;

DESVAUX, H ;

MANSUY, D ;

TRAYLOR, TG .

TETRAHEDRON LETTERS, 1991, 32 (25) :2893-2896

[2] Poly(ethylene glycol)-supported tetrahydroxyphenyl porphyrin: A convenient, recyclable catalyst for photooxidation reactions [J].

Benaglia, M ;

Danelli, T ;

Fabris, F ;

Sperandio, D ;

Pozzi, G .

ORGANIC LETTERS, 2002, 4 (24) :4229-4232

[3] Efficient microwave-assisted synthesis of new sulfonylbenzimidazole-4,7-diones: heterocyclic quinones with potential antitumor activity [J].

Boufatah, N ;

Gellis, A ;

Maldonado, J ;

Vanelle, P .

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 [J].

Chen, X ;

Hui, L ;

Foster, DA ;

Drain, CM .

BIOCHEMISTRY, 2004, 43 (34) :10918-10929

[6] A perspective on four new porphyrin-based functional materials and devices [J].

Drain, CM ;

Hupp, JT ;

Suslick, KS ;

Wasielewski, MR ;

Chen, X .

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2002, 6 (04) :243-258

[7] Synthesis of meso substituted porphyrins in air without solvents or catalysts [J].

Drain, CM ;

Gong, XC .

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 [J].

Liu, MO ;

Hu, AT .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (15) :2450-2455

[10] Microwave-assisted synthesis and reverse saturable absorption of phthalocyanines and porphyrins [J].

Liu, MO ;

Tai, CH ;

Wang, WY ;

Chen, JR ;

Hu, AT ;

Wei, TH .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (06) :1078-1084