Polystyrene-supported Pd(II)-N-heterocyclic carbene complex as a heterogeneous and recyclable precatalyst for cross-coupling of acyl chlorides with arylboronic acids

被引：10

作者：

Movassagh, Barahman ^{[1
]}

Hajizadeh, Fatemeh ^{[1
]}

Mohammadi, Elmira ^{[1
]}

机构：

[1] KN Toosi Univ Technol, Dept Chem, POB 16315-1618, Tehran, Iran

来源：

APPLIED ORGANOMETALLIC CHEMISTRY | 2018年 / 32卷 / 01期

关键词：

aroyl chlorides; arylboronic acids; diaryl ketones; heterogeneous catalysis; palladium-catalysed; ONE-POT SYNTHESIS; CATALYZED DIRECT CONVERSION; CARBOXYLIC ANHYDRIDES; ARYL KETONES; HECK REACTION; ORGANOBORON COMPOUNDS; ORGANOZINC REAGENTS; EFFICIENT SYNTHESIS; NEUTRAL CONDITIONS; CARBON NANOTUBES;

D O I：

10.1002/aoc.3982

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Palladium-catalysed cross-coupling reaction of aroyl chlorides with arylboronic acids was achieved in the presence of polystyrene-supported palladium(II)-N-heterocyclic carbene complex, using K2CO3 in acetone-water, providing diaryl ketones in high yields. Furthermore, the heterogeneous catalyst could be reused up to four times without significant loss of activity.

引用

页数：6

共 69 条

[1] Tris(perfluoroalkyl)silyl entities as unexpectedly potent tags for the noncovalent immobilization of catalysts by fluorous-fluorous interactions:: Application to the synthesis of several perfluoro-tagged ligands [J].

Andrushko, V ;

Schwinn, D ;

Tzschucke, CC ;

Michalek, F ;

Horn, J ;

Mössner, C ;

Bannwarth, W .

HELVETICA CHIMICA ACTA, 2005, 88 (05) :936-949

[2] Lewis acid-promoted coupling reactions of acid chlorides with organoaluminum and organozinc reagents [J].

Arisawa, M ;

Torisawa, Y ;

Kawahara, M ;

Yamanaka, M ;

Nishida, A ;

Nakagawa, M .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (13) :4327-4329

[3]

Baggett S, 2005, STUD NAT PROD CHEM, V32, P721

[4] A rapid, solvent-free, ligandless and mild method for preparing aromatic ketones from acyl chlorides and arylboronic acids via a Suzuki-Miyaura type of coupling reaction [J].

Bandgar, BP ;

Patil, AV .

TETRAHEDRON LETTERS, 2005, 46 (44) :7627-7630

[5] Carbonylative Suzuki-Miyaura Coupling of Arylboronic Acids with Aryl Iodides Catalyzed by the MCM-41-Supported Bidentate Phosphane Palladium(II) Complex [J].

Cai, Mingzhong ;

Zheng, Guomin ;

Zha, Lingfang ;

Peng, Jian .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (10) :1585-1591

[6] Silica-supported phosphine palladium(0) complex catalyzed phenylation of acid chlorides and aryl iodides by sodium tetraphenylborate [J].

Cai, MZ ;

Song, CS ;

Huang, X .

SYNTHETIC COMMUNICATIONS, 1998, 28 (04) :693-700

[7] Concentrations of the sunscreen agent benzophenone-3 in residents of the United States: National Health and Nutrition Examination Survey 2003-2004 [J].

Calafat, Antonia M. ;

Wong, Lee-Yang ;

Ye, Xiaoyun ;

Reidy, John A. ;

Needham, Larry L. .

ENVIRONMENTAL HEALTH PERSPECTIVES, 2008, 116 (07) :893-897

[8] Hierarchical Structures of Polystyrene-block-poly(2-vinylpyridine)/Palladium-Pincer Surfactants: Effect of Weak Surfactant-Polymer Interactions on the Morphological Behavior [J].

Davidi, Inbal ;

Patra, Debabrata ;

Herrnida-Merino, Daniel ;

Portale, Giuseppe ;

Rotello, Vincent M. ;

Raviv, Uri ;

Shenhar, Roy .

MACROMOLECULES, 2014, 47 (16) :5774-5783

[9] A new efficient synthesis of pyridines [J].

DeKimpe, N ;

Keppens, M ;

Fonck, G .

CHEMICAL COMMUNICATIONS, 1996, (05) :635-636

[10] Anthraquinones with quinone reductase-inducing activity and Benzophenones from Morinda citrifolia (Noni) roots [J].

Deng, Ye ;

Chin, Young-Won ;

Chai, Heebyung ;

Keller, William J. ;

Kinghorn, A. Douglas .

JOURNAL OF NATURAL PRODUCTS, 2007, 70 (12) :2049-2052

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