Lowering the symmetry of difunctionalized coordination compounds via nucleophilic aromatic substitutions

被引：9

作者：

Hurley, DJ ^{[1
]}

Tor, Y ^{[1
]}

机构：

[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 41期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(01)01540-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ru-11-coordinated 3,8-dibromo-1,10-phenanthroline undergoes nucleophilic aromatic substitutions with simple nucleophiles (e.g. thiolate) to give the disubstituted products in high yields. When a fluorenyl anion is used, a mono-substituted product is exclusively obtained. The highly acidic nature of this mono-substituted complex results in deprotonation under the reaction conditions and deactivation toward a second substitution reaction. A complex of lower symmetry that can be further functionalized using other transformations is obtained. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：7217 / 7220

页数：4

共 26 条

[11]

Edwards PG, 2000, ANGEW CHEM INT EDIT, V39, P2922, DOI 10.1002/1521-3773(20000818)39:16<2922::AID-ANIE2922>3.0.CO

[12]

2-S

[13] Base-promoted hydroalkylation reactions of 1,3,5-Me3C6H3, p-MeC6H4CHMe2, C6Me6, p-MeC6H4Me, and MeC6H5 ligands coordinated to ruthenium(II) [J].

Ghebreyessus, KY ;

Nelson, JH .

ORGANOMETALLICS, 2000, 19 (17) :3387-3392

[14] OPTICALLY ACTIVE CO-ORDINATION COMPOUNDS .20. REACTIONS OF 1,10-PHENANTHROLINE CO-ORDINATED TO COBALT(III) [J].

GILLARD, RD ;

HILL, REE ;

MASKILL, R .

JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1970, (09) :1447-&

[15] Coordination compounds as building blocks:: simple synthesis of RuII-containing amino acids and peptides [J].

Hurley, DJ ;

Roppe, JR ;

Tor, Y .

CHEMICAL COMMUNICATIONS, 1999, (11) :993-994

[16] EFFECT OF COORDINATION ON THE RATE OF METHOXYDECHLORINATION OF 5-CHLORO-1,10-PHENANTHROLINE [J].

JACKSON, K ;

RIDD, JH ;

TOBE, ML .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1979, (05) :611-617

[17] Total synthesis of the cyclic biphenyl ether peptides K-13 and OF4949-III via SNAr macrocyclization of peptidyl ruthenium pi-arene complexes [J].

Janetka, JW ;

Rich, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (28) :6488-6495

[18]

Jones MM, 1968, LIGAND REACTIVITY CA

[19]

KOSOWER EM, 1967, INTRO PHYSICAL ORGAN, V89, P2752

[20] Approaches to the fully functionalized DEF ring system of ristocetin A via highly selective ruthenium-promoted SNAr reaction [J].

Pearson, AJ ;

Heo, JN .

ORGANIC LETTERS, 2000, 2 (19) :2987-2990

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