SNAr reactions of β-substituted porphyrins and the synthesis of meso substituted tetrabenzoporphyrins

被引：26

作者：

Senge, MO ^{[1
]}

Bischoff, I ^{[1
]}

机构：

[1] Univ Potsdam, Inst Chem, D-14476 Golm, Germany

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 08期

关键词：

nucleophilic aromatic substitution; tetrabenzoporphyrins; C-C coupling reactions; organolithium reagents; tetrapyrroles;

D O I：

10.1016/j.tetlet.2003.12.121

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of 2,3.7,8,12,13,17,18-octaethylporphyrin with LiR reagents containing functional groups readily yields meso substituted derivatives suitable for further transformations with residues such as -p-C6H5Br, -p-C6H5-C=CH -p-C6H5-NH2 or -(CH2)(3)-CH=CH2. Similar reactions of tetrabenzoporphyrin with alkyllithium reagents afforded the first entry into meso mono- and dialkylsubstituted tetrabenzoporphyrins while reaction of bicyclo[2.2.2]oct-type masked isoindole precursors with LiR followed by in situ retro-Diels-Alder reaction also afforded the 5-phenyl and 5,10-diphenyltetrabenzoporphyrins in high purity. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：1647 / 1650

页数：4

共 16 条

[1] Mechanistic studies on the nucleophilic reaction of porphyrins with organolithium reagents [J].