Palladium-ADC complexes as efficient catalysts in copper-free and room temperature Sonogashira coupling

被引：51

作者：

Valishina, Elena A. ^{[1
,2
]}

Guedes da Silva, M. Fatima C. ^{[2
,3
]}

Kinzhalov, Mikhail A. ^{[4
]}

Timofeeva, Svetlana A. ^{[4
]}

Buslaeva, Tatyana M. ^{[1
]}

Haukka, Matti ^{[5
]}

Pombeiro, Armando J. L. ^{[2
]}

Boyarskiy, Vadim P. ^{[4
]}

Kukushkin, Vadim Yu. ^{[4
]}

Luzyanin, Konstantin V. ^{[4
]}

机构：

[1] Moscow State Univ Fine Chem Technol, Moscow 119571, Russia

[2] Univ Lisbon, Inst Super Tecn, Ctr Quim Estrutural, P-1049001 Lisbon, Portugal

[3] Univ Lusofona Humanidades & Tecnol, ULHT Lisbon, P-1749024 Lisbon, Portugal

[4] St Petersburg State Univ, Dept Chem, St Petersburg 198504, Russia

[5] Univ Jyvaskyla, Dept Chem, FI-40014 Jyvaskyla, Finland

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2014年 / 395卷

关键词：

Acyclic diaminocarbenes; Palladium-(acyclic diminocarbene) catalysts; Metal-mediated coupling; Isocyanides; Sonogashira cross-coupling; N-HETEROCYCLIC CARBENES; PROMOTED CYCLIZATION REACTIONS; ONE-POT SYNTHESIS; X-RAY; ACYCLIC DIAMINOCARBENES; ISOCYANIDE COMPLEXES; NEUTRON-DIFFRACTION; BOND LENGTHS; LIGANDS; ISONITRILES;

D O I：

10.1016/j.molcata.2014.08.018

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The metal-mediated coupling between cis-[PdCl2(CNR1)(2)] [R-1 = cyclohexyl (Cy) 1, t-Bu 2, 2,6-Me2C6H3 (Xyl) 3, 2-Cl-6-MeC6H3 4] and hydrazones H2NNCR2R3 [R-2, R-3 = Ph 5; R-2, R-3 = C6H4(OMe-4) 6; R-2/R-3 = 9-fluorenyl 7; R-2 = H, R-3 = C6H4(OH-2) 8] provided carbene complexes cis-[PdCl2{C(N(H)N=CR2R3)N(H)R-1}(CNR1)] (9-24) in good (80-85%) yields. Complexes 9-24 showed high activity [yields up to 99%, and turnover numbers (TONs) up to 3.7 x 10(4)] in the Sonogashira coupling of various aryl iodides with a range of substituted aromatic alkynes without the need of copper co-catalyst. The catalytic procedure runs at 80 degrees C for 1 h in EtOH using K2CO3 as a base. No formation of homocoupling or acetylene decomposition products was observed. Designed copper-free Sonogashira system can also run at room temperature giving target products with yields up to 87% and TONs up to 87. (C) 2014 Elsevier B.V. All rights reserved.

引用

页码：162 / 171

页数：10

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