Copper- and ligand-free sonogashira reaction catalyzed by Pd(0) nanoparticles at ambient conditions under ultrasound irradiation

被引：181

作者：

Gholap, AR

Venkatesan, K

Pasricha, R

Daniel, T

Lahoti, RJ

Srinivasan, KV

机构：

[1] Natl Chem Lab, Div Technol, Pune 411008, Maharashtra, India

[2] Natl Chem Lab, Ctr Mat Characterizat, Pune 411008, Maharashtra, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 12期

关键词：

D O I：

10.1021/jo0503815

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Sonogashira reaction proceeds at ambient temperature (30 degrees C) in acetone or room-temperature ionic liquid, 1,3-di-n-butylimidazolium tetrafluoroborate ([bbim]BF4), as solvent under ultrasound irradiation to give enhanced reaction rates, excellent chemoselectivity, and high yields in the absence of a copper cocatalyst and a phosphine ligand. TEM analysis showed the formation of stable, crystalline, and polydispersed Pd(0) nanoparticles as catalyst for the reaction.

引用

收藏

页码：4869 / 4872

页数：4

相关论文

共 56 条

[1] AN EFFICIENT PALLADIUM-CATALYZED REACTION OF VINYL AND ARYL HALIDES OR TRIFLATES WITH TERMINAL ALKYNES [J].

ALAMI, M ;

FERRI, F ;

LINSTRUMELLE, G .

TETRAHEDRON LETTERS, 1993, 34 (40) :6403-6406

[2] 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

[3]

Böhm VPW, 2000, EUR J ORG CHEM, V2000, P3679, DOI 10.1002/1099-0690(200011)2000:22<3679::AID-EJOC3679>3.0.CO

[4]

2-X

[5] Self-assembly of folded m-phenylene ethynylene oligomers into helical columns [J].

Brunsveld, L ;

Meijer, EW ;

Prince, RB ;

Moore, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (33) :7978-7984

[6] Catalytic coupling of terminal acetylenes with iodoarenes and diaryliodonium salts in water [J].

Bumagin, NA ;

Sukhomlinova, LI ;

Luzikova, EV ;

Tolstaya, TP ;

Beletskaya, IP .

TETRAHEDRON LETTERS, 1996, 37 (06) :897-900

[7] A copper- and amine-free sonogashira reaction employing aminophosphines as ligands [J].

Cheng, J ;

Sun, YH ;

Wang, F ;

Guo, MJ ;

Xu, JH ;

Pan, Y ;

Zhang, ZG .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) :5428-5432

[8] Layered double hydroxide supported nanopalladium catalyst for Heck-, Suzuki-, Sonogashira-, and Stille-type coupling reactions of chloroarenes [J].

Choudary, BM ;

Madhi, S ;

Chowdari, NS ;

Kantam, ML ;

Sreedhar, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (47) :14127-14136

[9] Synthesis of the C1′-C11′ oxazole-containing side chain of leucascandrolide A.: Application of a sonogashira cross-coupling [J].

Dakin, LA ;

Langille, NF ;

Panek, JS .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (19) :6812-6815

[10] Ultrasound promoted C-C bond formation: Heck reaction at ambient conditions in room temperature ionic liquids [J].

Deshmukh, RR ;

Rajagopal, R ;

Srinivasan, KV .

CHEMICAL COMMUNICATIONS, 2001, (17) :1544-1545

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