Dimethylaminoalkylchalcogenolate complexes of palladium(II): Synthesis, structures, and their catalytic activity in Suzuki C-C cross-coupling reactions

被引:23
作者
Paluru, Dilip K. [1 ]
Dey, Sandip [1 ]
Wadawale, Amey [1 ]
Jain, Vimal K. [1 ]
机构
[1] Bhabha Atom Res Ctr, Div Chem, Bombay 400085, Maharashtra, India
关键词
Palladium; Chalcogenolate; X-ray; Suzuki coupling; HETEROCYCLIC CARBENE LIGAND; ARYL CHLORIDES; ORGANIC TELLURIDES; PHENYLBORONIC ACID; AEROBIC CONDITIONS; CRYSTAL-STRUCTURES; ROOM-TEMPERATURE; HIGHLY EFFICIENT; MIYAURA REACTION; HECK REACTION;
D O I
10.1016/j.jorganchem.2013.01.008
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The reaction of [PdCl((EN)-N-boolean AND)](n) with AgOAc in methanol afforded the corresponding acetato complexes, [Pd(OAc)((EN)-N-boolean AND)](n) ((EN)-N-boolean AND/n = ECH2CH2NMe2/3; ECH2CH2CH2NMe2/2 (E = S or Se)). The molecular structures of [Pd(OAc)(ECH2CH2NMe2)](3) were established by single crystal X-ray diffraction analyses. The trimeric structures comprise of three palladium atoms bridged through chalcogen atoms of the chelating chalcogenolate ligand forming a twisted six-membered Pd3E3 ring. The acetato-ligand acts in a monodentate fashion. The catalytic activity of [PdCl((EN)-N-boolean AND)](n) and [Pd(OAc)((EN)-N-boolean AND)](n) in Suzuki C-C cross coupling reactions has been investigated. The dimeric acetato complexes showed the best activity in dioxane. (C) 2013 Elsevier B.V. All rights reserved.
引用
收藏
页码:52 / 56
页数:5
相关论文
共 57 条
[1]   An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature [J].
Altenhoff, G ;
Goddard, R ;
Lehmann, CW ;
Glorius, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3690-3693
[2]   COMPLETION AND REFINEMENT OF CRYSTAL-STRUCTURES WITH SIR92 [J].
ALTOMARE, A ;
CASCARANO, G ;
GIACOVAZZO, C ;
GUAGLIARDI, A .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1993, 26 (pt 3) :343-350
[3]   Toward the Ideal Catalyst: From Atomic Centers to a "Cocktail" of Catalysts [J].
Ananikov, Valentine P. ;
Beletskaya, Irina P. .
ORGANOMETALLICS, 2012, 31 (05) :1595-1604
[4]   Isolation of an [SNS]Pd(II) pincer with a water ladder and its Suzuki coupling activity in water [J].
Bai, Shi-Qiang ;
Hor, T. S. Andy .
CHEMICAL COMMUNICATIONS, 2008, (27) :3172-3174
[5]   Non-trivial behavior of palladium(II) acetate [J].
Bakhmutov, VI ;
Berry, JF ;
Cotton, FA ;
Ibragimov, S ;
Murillo, CA .
DALTON TRANSACTIONS, 2005, (11) :1989-1992
[6]   Di- and tri-alkylphosphine adducts of S-donor palladacycles as catalysts in the Suzuki coupling of aryl chlorides [J].
Bedford, RB ;
Cazin, CSJ ;
Hursthouse, MB ;
Light, ME ;
Scordia, EJM .
DALTON TRANSACTIONS, 2004, (22) :3864-3868
[7]   Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters [J].
Billingsley, Kelvin ;
Buchwald, Stephen L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) :3358-3366
[8]   Selenoether ligand assisted Heck catalysis [J].
Chakraborty, Tapash ;
Srivastava, Kriti ;
Singh, Harkesh B. ;
Butcher, Ray J. .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (13) :2559-2564
[9]   Reactions of Di-o-tolyl Telluride and Selenide with Palladium Acetate: Isolation of a Novel Palladium Complex of a Tellurenic Acid Anhydride and Related Trinuclear and Tetranuclear Palladium Complexes [J].
Chakraborty, Tapash ;
Sharma, Sagar ;
Singh, Harkesh B. ;
Butcher, Ray J. .
ORGANOMETALLICS, 2011, 30 (09) :2525-2530
[10]   Isolation of chloro-bridged arylpalladium complexes, [Pd2Ar2(μ-Cl)2(PR3)2], in palladium catalyzed C-C cross coupling reaction of triarylbismuth with arylhalides [J].
Chaudhari, Kamal R. ;
Wadawale, Amey P. ;
Jain, Vimal K. .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 698 :15-21