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

[11]

Senge MO, 2000, CHEM-EUR J, V6, P2721

[12]

Senge MO, 2001, EUR J ORG CHEM, V2001, P1735

[13]

Vicente M. G. H., 2000, The Porphyrin Handbook-Synthesis and Organic Chemistry, V1, P149

[14] Synthesis and chemistry of new benzoporphyrins [J].

Vicente, MGH ;

Jaquinod, L ;

Khoury, RG ;

Madrona, AY ;

Smith, KM .

TETRAHEDRON LETTERS, 1999, 40 (50) :8763-8766

[15] Palladium catalyzed carbonylation of Br-substituted porphyrins [J].

Vinogradov, SA ;

Wilson, DF .

TETRAHEDRON LETTERS, 1998, 39 (49) :8935-8938

[16] SIMPLE TEMPLATE SYNTHESIS OF ZINC TETRABENZPORPHYRIN [J].

VOGLER, A ;

KUNKELY, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (10) :760-760

← 1 2 →