Efficient Synthesis of Hangman Porphyrins

被引：47

作者：

Dogutan, Dilek K. ^{[1
]}

Bediako, D. Kwabena ^{[1
]}

Teets, Thomas S. ^{[1
]}

Schwalbe, Matthias ^{[1
]}

Nocera, Daniel G. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 05期

关键词：

COUPLED ELECTRON-TRANSFER; BRIDGED COFACIAL BISPORPHYRINS; MICROWAVE-ASSISTED SYNTHESIS; O BOND ACTIVATION; MESO SUBSTITUENTS; SOLAR-ENERGY; COMPOUND-I; XANTHENE; BEARING; ARCHITECTURES;

D O I：

10.1021/ol902947h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A two-step synthetic method has been designed to furnish hangman porphyrins in good yields from easily available starting materials. The use of the microwave irradiation technique has been found to be valuable for delivering the carboxylic acid hanging group in a much simplified and less time-consuming basic ester hydrolysis (4 h vs 7 days under harsh acidic conditions). The new route facilitates the synthesis of various hangman porphyrins that previously had limited or no access.

引用

收藏

页码：1036 / 1039

页数：4

相关论文

共 42 条

[1] Metal catalyst-free amination of meso-bromoporphyrins: an entry to supramolecular porphyrinoid frameworks [J].

Balaban, Mihaela Carmen ;

Chappaz-Gillot, Cyril ;

Canard, Gabriel ;

Fuhr, Olaf ;

Roussel, Christian ;

Balaban, Teodor Silviu .

TETRAHEDRON, 2009, 65 (18) :3733-3739

[2] Proton-coupled O-O activation on a redox platform bearing a hydrogen-bonding scaffold [J].

Chang, CJ ;

Chng, LL ;

Nocera, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (07) :1866-1876

[3] Electrocatalytic four-electron reduction of oxygen to water by a highly flexible cofacial cobalt bisporphyrin [J].

Chang, CJ ;

Deng, YQ ;

Shi, CN ;

Chang, CK ;

Anson, FC ;

Nocera, DG .

CHEMICAL COMMUNICATIONS, 2000, (15) :1355-1356

[4] Xanthene-bridged cofacial bisporphyrins [J].

Chang, CJ ;

Deng, YQ ;

Heyduk, AF ;

Chang, CK ;

Nocera, DG .

INORGANIC CHEMISTRY, 2000, 39 (05) :959-966

[5] Porphyrin architectures bearing functionalized xanthene spacers [J].

Chang, CJ ;

Yeh, CY ;

Nocera, DG .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) :1403-1406

[6] Porphyrin xanthene amides: anchoring distal H-bonding in heme models [J].

Chang, CK ;

Bag, N ;

Guo, BM ;

Peng, SM .

INORGANICA CHIMICA ACTA, 2003, 351 :261-268

[7] Proton transfer at helium temperatures during dioxygen activation by heme monooxygenases [J].

Davydov, R ;

Chemerisov, S ;

Werst, DE ;

Rajh, T ;

Matsui, T ;

Ikeda-Saito, M ;

Hoffman, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (49) :15960-15961

[8] Microwave-promoted insertion of Group 10 metals into free base porphyrins and chlorins:: scope and limitations [J].

Dean, Michelle L. ;

Schmink, Jason R. ;

Leadbeater, Nicholas E. ;

Bruckner, Christian .

DALTON TRANSACTIONS, 2008, 10 (10) :1341-1345

[9] Molecular chemistry of consequence to renewable energy [J].

Dempsey, JL ;

Esswein, AJ ;

Manke, DR ;

Rosenthal, J ;

Soper, JD ;

Nocera, DG .

INORGANIC CHEMISTRY, 2005, 44 (20) :6879-6892

[10] Direct observation of the "Pac-Man" effect from dibenzofuran-bridged cofacial bisporphyrins [J].

Deng, YQ ;

Chang, CJ ;

Nocera, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (02) :410-411

← 1 2 3 4 5 →