Microwave-promoted Suzuki-Miyaura cross-coupling of aryl halides with phenylboronic acid under aerobic conditions catalyzed by a new palladium complex with a thiosemicarbazone ligand

被引：63
作者：
Kostas, Ioannis D.
Heropoulos, Georgios A.
Kovala-Demertzi, Dimitra
Yadav, Paras N.
Jasinski, Jerry P.
Demertzis, Mavroudis A.
Andreadaki, Fotini J.
Vo-Thanh, Giang
Petit, Alain
Loupy, Andre
机构：
[1] Natl Hellen Res Fdn, Inst Organ & Pharmaceut Chem, Athens 11635, Greece
[2] Univ Ioannina, Dept Chem, Sector Inorgan & Analyt Chem, GR-45110 Ioannina, Greece
[3] Keene State Coll, Dept Chem, Keene, NH 03435 USA
[4] Univ Paris 11, ICMMO, Lab React Select Supports, F-91405 Orsay, France
来源：
TETRAHEDRON LETTERS | 2006年 / 47卷 / 26期
关键词：
thiosemicarbazone; Suzuki-Miyaura cross-coupling; microwave; phosphine-free ligand; C-C bond formations; homogeneous catalysis;
D O I：
10.1016/j.tetlet.2006.04.088
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new air- and moisture-stable palladium complex with salicylaldehyde N(4)-hexamethyleneiminylthiosemicarbazone has been synthesized. According to its crystal structure, the metal is bonded to 2 equiv monoanionic thiosemicarbazone moieties in a N,S-bidentate fashion, forming two five-membered chelate rings. while additional intramolecular bonds stabilize the structure. In contrast to other palladium complexes with thiosemicarbazones. this complex was inactive towards the Suzuki-Miyaura coupling under aerobic conditions, by conventional heating. On the other hand. microwave irradiation promoted the effective catalytic activity of the complex for the coupling of aryl bromides and chlorides with phenylboronic acid in DMF/H2O, under aerobic conditions, with turnover numbers of up to 37,000. (c) 2006 Elsevier Ltd. All rights reserved.
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页码：4403 / 4407
页数：5
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