Synthesis of chlorinated biphenyls by Suzuki cross-coupling using diamine or diimine-palladium complexes

被引：71

作者：

Kylmala, Tuula ^{[1
]}

Kuuloja, Noora ^{[1
]}

Xu, Youjun ^{[2
]}

Rissanen, Kari ^{[3
]}

Franzen, Robert ^{[1
]}

机构：

[1] Tampere Univ Technol, Dept Chem & Bioengn, Hermiankatu 7D,POB 541, Tampere 33720, Finland

[2] Shenyang Pharmaceut Univ, Sch Pharmaceut Engn, Shenyang 110016, Peoples R China

[3] Univ Jyvaskyla, Nanosci Ctr, Dept Chem, Jyvaskyla 40014, Finland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 23期

基金：

芬兰科学院;

关键词：

diimine ligands; diamine ligands; palladium complexes; Suzuki cross-coupling; biaryl compounds; polychlorinated biphenyls (PCBs); biphenylcarboxylic acids (BCAs); Suzuki reaction;

D O I：

10.1002/ejoc.200800119

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several novel diimines (Salen-type ligands) 2a-2i and their reduced diamine counterparts 3b,3d-3g and 3i form complexes 4a-4i, 5b,5d-5g, and 5i with PdCl2 in DMF or methanol. Using 1 mol-% of the isolated complexes 4e and 5f many polychlorinated biphenyls (PCBs) can be prepared in moderate to excellent yields according to the Suzuki cross-coupling protocol with contact to air. Several 4-acetylbiphenyls prepared by this method can be converted in moderate yields into the corresponding biphenylcarboxylic acids (BCAs) by alkaline cleavage. An X-ray crystal structure determination confirms the structure of complex 5f. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

引用

页码：4019 / 4024

页数：6

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