A palladium salen complex: an efficient catalyst for the Sonogashira reaction at room temperature

被引:31
作者
Gogoi, Ankur [1 ]
Dewan, Anindita [1 ,2 ]
Borah, Geetika [1 ]
Bora, Utpal [1 ,2 ]
机构
[1] Dibrugarh Univ, Dept Chem, Dibrugarh 786004, Assam, India
[2] Tezpur Univ, Dept Chem Sci, Tezpur 784028, Assam, India
关键词
COPPER-FREE; COUPLING REACTIONS; TERMINAL ALKYNES; ARYL BROMIDES; LIGAND-FREE; SUZUKI; PALLADACYCLE; IODIDES; HIYAMA; WATER;
D O I
10.1039/c4nj01822b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A tetradentate Schiff base derived palladium complex has been developed as a catalyst for the room temperature Sonogashira reaction under copper free conditions. The main catalytic species, a Pd-complex was derived from Schiff base ligand N,N'-bis(salicylidene)-aryl-methanediamine and Pd(OAc)(2). Electron rich, electron deficient and sterically hindered aryl iodides underwent smooth coupling to afford good to excellent yield of diaryl alkynes in isopropanol at room temperature. The protocol is also suitable for aliphatic alkynes.
引用
收藏
页码:3341 / 3344
页数:4
相关论文
共 47 条
[1]   Oxime palladacycles:: Stable and efficient catalysts for carbon-carbon coupling reactions [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
ORGANIC LETTERS, 2000, 2 (13) :1823-1826
[2]   C(sp2)-C(sp) and C(sp)-C(sp) coupling reactions catalyzed by oxime-derived palladacycles [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (9-10) :1146-1158
[3]   A copper- and amine-free Sonogashira-type coupling procedure catalyzed by oxime palladacycles [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
TETRAHEDRON LETTERS, 2002, 43 (51) :9365-9368
[4]   Copper- and phosphine-free Sonogashira coupling reactions of aryl iodides catalyzed by an N,N-bis(naphthylideneimino)diethylenetriamine-functionalized polystyrene resin supported Pd(II) complex under aerobic conditions [J].
Bakherad, Mohammad ;
Amin, Amir H. ;
Keivanloo, Ali ;
Bahramian, Bahram ;
Raeissi, Mersad .
TETRAHEDRON LETTERS, 2010, 51 (43) :5653-5656
[5]   Copper-free Sonogashira coupling reactions catalyzed by a water-soluble Pd-salen complex under aerobic conditions [J].
Bakherad, Mohammad ;
Keivanloo, Ali ;
Bahramian, Bahram ;
Hashemi, Mahdieh .
TETRAHEDRON LETTERS, 2009, 50 (14) :1557-1559
[6]   Palladium(II) complex with a potential N4-type Schiff-base ligand as highly efficient catalyst for Suzuki-Miyaura reactions in aqueous media [J].
Banik, Biplab ;
Tairai, Archana ;
Shahnaz, Nasifa ;
Das, Pankaj .
TETRAHEDRON LETTERS, 2012, 53 (42) :5627-5630
[7]   Phosphine-free Pd-salen complexes as efficient and inexpensive catalysts for Heck and Suzuki reactions under aerobic conditions [J].
Borhade, Sanjay R. ;
Waghmode, Suresh B. .
TETRAHEDRON LETTERS, 2008, 49 (21) :3423-3429
[8]   Recyclable Hybrid Silica-Based Catalysts Derived from Pd-NHC Complexes for Suzuki, Heck and Sonogashira Reactions [J].
Borja, Guadalupe ;
Monge-Marcet, Amalia ;
Pleixats, Roser ;
Parella, Teodor ;
Cattoen, Xavier ;
Man, Michel Wong Chi .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (19) :3625-3635
[9]   Bis(pyrimidine)-based palladium catalysts: synthesis, X-ray structure and applications in Heck-, Suzuki-, Sonogashira-Hagihara couplings and amination reactions [J].
Buchmeiser, MR ;
Schareina, T ;
Kempe, R ;
Wurst, K .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 634 (01) :39-46
[10]   Poly(aryleneethynylene)s: Syntheses, properties, structures, and applications [J].
Bunz, UHF .
CHEMICAL REVIEWS, 2000, 100 (04) :1605-1644