Water-promoted palladium-catalysed Heck cross-coupling reactions of aryl halides with alkenes in TBAB

被引：13

作者：

Tao, Li-Ming ^{[1
]}

Li, Qiang-Guo ^{[1
]}

Liu, Wen-Qi ^{[1
]}

Zhou, Yun ^{[1
]}

Zhou, Ju-Feng ^{[1
]}

机构：

[1] Xiangnan Univ, Dept Chem & Life Sci, Chenzhou 423000, Peoples R China

来源：

JOURNAL OF CHEMICAL RESEARCH | 2011年 / 03期

基金：

中国国家自然科学基金;

关键词：

Pd(OAc)(2); H2O; TBAB; Heck coupling reaction; IONIC LIQUIDS; EFFICIENT; LIGAND; MICROWAVE; COMPLEXES; CARBON; SUZUKI; BASE;

D O I：

10.3184/174751911X12979690024078

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Water was found to promote the ligand-free Pd(OAc)(2)-catalysed Heck cross-coupling reaction. In the presence of 3 mol% Pd(OAc)(2), 2 equiv. of Cs2CO3 and 15 mg of water, the coupling of a wide variety of aryl halides with alkenes proceeded smoothly in TBAB (n-Bu4NBr) in moderate to excellent yield. The Pd(OAc)(2)/TBAB system could be recovered and reused at least three times without loss of catalytic activity.

引用

页码：154 / 156

页数：3

共 23 条

[1] Rate and mechanism of the reaction of alkenes with aryl palladium complexes ligated by a bidentate PP ligand in Heck reactions [J].

Amatore, Christian ;

Godin, Beatrice ;

Jutand, Anny ;

Lemaitre, Frederic .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (07) :2002-2011

[2] Application of microwave irradiation to phase-transfer catalyzed reactions [J].

Bogdal, Dariusz ;

Loupy, Andre .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2008, 12 (04) :710-722

[3] Manganese-Catalyzed Cross-Coupling Reaction between Aryl Grignard Reagents and Alkenyl Halides [J].

Cahiez, Gerard ;

Gager, Olivier ;

Lecomte, Fabien .

ORGANIC LETTERS, 2008, 10 (22) :5255-5256

[4] Ligandless, Anionic, Arylpalladium Halide Intermediates in the Heck Reaction [J].

Carrow, Brad P. ;

Hartwig, John. F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (01) :79-+

[5] Efficient, Regioselective Palladium-Catalyzed Tandem Heck-Isomerization Reaction of Aryl Bromides and Non-Allylic Benzyl Alcohols [J].

Crawley, Matthew L. ;

Phipps, Kristin M. ;

Goljer, Igor ;

Mehlmann, John F. ;

Lundquist, Joseph T. ;

Ullrich, John W. ;

Yang, Cuijian ;

Mahaney, Paige E. .

ORGANIC LETTERS, 2009, 11 (05) :1183-1185

[6] Soluble polysiloxane-supported palladium catalysts for the Mizoroki-Heck reaction [J].

Cypryk, Marek ;

Pospiech, Piotr ;

Strzelec, Krzysztof ;

Wasikowska, Karolina ;

Sobczak, Janusz W. .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2010, 319 (1-2) :30-38

[7] Palladium(II) Complexes of the First Pincer (Se,N,Se) Ligand, 2,6-Bis((phenylseleno)methyl)pyridine (L): Solvent-Dependent Formation of [PdCl(L)]Cl and Na[PdCl(L)][PdCl4] and High Catalytic Activity for the Heck Reaction [J].

Das, Dipanwita ;

Rao, G. K. ;

Singh, Ajai K. .

ORGANOMETALLICS, 2009, 28 (20) :6054-6058

[8] A Concise Approach to the Synthesis of opp-Dibenzoporphyrins through the Heck Reaction [J].

Deshpande, Rohit ;

Jiang, Lin ;

Schmidt, Gregory ;

Rakovan, John ;

Wang, Xiaoping ;

Wheeler, Kraig ;

Wang, Hong .

ORGANIC LETTERS, 2009, 11 (19) :4251-4253

[9] Bronsted guanidine acid-base ionic liquids: Novel reaction media for the palladium-catalyzed Heck reaction [J].

Li, SH ;

Lin, YJ ;

Xie, HB ;

Zhang, SB ;

Xu, JN .

ORGANIC LETTERS, 2006, 8 (03) :391-394

[10] Palladium-catalyzed reduction of alkynes employing HSiEt3: stereoselective synthesis of trans- and cis-alkenes [J].

Luo, Fang ;

Pan, Changduo ;

Wang, Wenhui ;

Ye, Zhishi ;

Cheng, Jiang .

TETRAHEDRON, 2010, 66 (06) :1399-1403

← 1 2 3 →