Fluoroalkylation of porphyrins:: Synthesis of porphyrins bearing double meso,β-fused fluoroalkyl rings via radical cyclization

被引：9

作者：

Chen, Liang

Jin, Li-Mei

Xiao, Ji-Chang

Guo, Can-Cheng

Chen, Qing-Yun ^{[1
]}

机构：

[1] Hunan Univ, Coll Chem & Chem Engn, Changsha 410082, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

来源：

SYNLETT | 2007年 / 13期

关键词：

fluoroalkylation; fused porphyrins; radical cyclization; fluoroalkyl iodides; sulfinatodehalogenation;

D O I：

10.1055/s-2007-984888

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of fluorinated meso,beta-fused 5,15-diphenyl-porphyrins have been synthesized by the reaction of 5,15-diphenylporphyrins with fluoroalkyl halides under modified sulfinatodehalogenation reaction conditions through radical cyclization.

引用

页码：2096 / 2100

页数：5

共 15 条

[1] 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

[2] Fluoroalkylation of porphyrins: Generation of 2-and 20-perfluoroalkyl-5,10,15-triarylporphyrin radicals and their intramolecular cyclizations [J].

Chen, L ;

Jin, LM ;

Guo, CC ;

Chen, QY .

SYNLETT, 2005, (06) :963-970

[3] 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

[4] Porphyrins with exocyclic rings. Part 20: Synthesis and spectroscopic characterization of porphyrins with fused 2,1,3-benzoxadiazole and 2,1,3-benzoselenadiazole moieties [J].

Cillo, CM ;

Lash, TD .

TETRAHEDRON, 2005, 61 (49) :11615-11627

[5] 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

[6] Synthetic routes to porphyrins bearing fused rings [J].

Fox, Simon ;

Boyle, Ross W. .

TETRAHEDRON, 2006, 62 (43) :10039-10054

[7] PERFLUOROALKYLATION INITIATED WITH SODIUM DITHIONITE AND RELATED REAGENT SYSTEMS [J].

HUANG, WY .

JOURNAL OF FLUORINE CHEMISTRY, 1992, 58 (01) :1-8

[8] Fluoroalkylation of porphyrins:: Preparation and characterization of meso- and β-fluoroalkyl-5,15-diarylporphyrins [J].

Jin, LM ;

Chen, L ;

Yin, JJ ;

Guo, CC ;

Chen, QY .

JOURNAL OF FLUORINE CHEMISTRY, 2005, 126 (9-10) :1321-1326

[9] Electrospray ionization (ESI) tandem mass spectrometric analysis of meso-tetrakis(heptafluoropropyl)Porphyrin [J].

Lau, KSF ;

Sadilek, M ;

Khalil, GE ;

Gouterman, M ;

Brückner, C .

JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 2005, 16 (12) :1915-1920

[10] The activation of carbon-chlorine bonds in per- and polyfluoroalkyl chlorides: DMSO-induced hydroperfluoroalkylation of alkenes and alkynes with sodium dithionite [J].

Long, ZY ;

Chen, QY .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4775-4782

← 1 2 →