Palladium-Catalyzed Cross-Coupling of Styrenes with Aryl Methyl Ketones in Ionic Liquids: Direct Access to Cyclopropanes

被引：43
作者：
Cotugno, Pietro [1 ]
Monopoli, Antonio [1 ]
Ciminale, Francesco [1 ]
Milella, Antonella [1 ]
Nacci, Angelo [1 ,2 ]
机构：
[1] Univ Bari, Dept Chem, I-70126 Bari, Italy
[2] Univ Bari, Dept Chem, CNR ICCOM, I-70126 Bari, Italy
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 49期
关键词：
C-H activation; copper; cyclopropanation; ionic liquids; palladium; CONTAINING NATURAL-PRODUCTS; DERIVATIVES; MECHANISM; OLEFINS;
D O I：
10.1002/anie.201408245
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The combined use of Pd(OAc)(2), Cu(OAc)(2), and dioxygen in molten tetrabutylammonium acetate (TBAA) promotes an unusual cyclopropanation reaction between aryl methyl ketones and styrenes. The process is a dehydrogenative cyclizing coupling that involves a twofold C H activation at the a-position of the ketone. The substrate scope highlights the flexibility of the catalyst; a reaction mechanism is also proposed.
引用
收藏
页码：13563 / 13567
页数：5
相关论文
共 27 条
[1]   Synthesis and bio-evaluation of alkylaminoaryl phenyl cyclopropyl methanones as antitubercular and antimalarial agents [J].
Ajay, Arya ;
Singh, Vandana ;
Singh, Shubhra ;
Pandey, Swaroop ;
Gunjan, Sarika ;
Dubey, Divya ;
Sinha, Sudhir Kumar ;
Singh, Bhupendra N. ;
Chaturvedi, Vinita ;
Tripathi, Renu ;
Ramchandran, Ravishankar ;
Tripathi, Rama P. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (23) :8289-8301
[2]  
[Anonymous], 2009, ANGEW CHEM
[3]   Rhodium-catalyzed synthesis of 2,3-diaryl-1,4-diketones via oxidative coupling of benzyl ketones using α-thioketone oxidizing reagent [J].
Arisawa, Mieko ;
Li, Guangzhe ;
Yamaguchi, Masahiko .
TETRAHEDRON LETTERS, 2013, 54 (10) :1298-1301
[4]   Natural occurrence, syntheses, and applications of cyclopropyl-group-containing α-amino acids.: 1.: 1-aminocyclopropanecarboxylic acid and other 2,3-methanoamino acids [J].
Brackmann, Farina ;
de Meijere, Armin .
CHEMICAL REVIEWS, 2007, 107 (11) :4493-4537
[5]   Pd-benzothiazol-2-ylidene complex in ionic liquids:: Efficient catalyst for carbon-carbon coupling reactions [J].
Calò, V ;
Nacci, A ;
Monopoli, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (24-25) :5458-5466
[6]   Stereoselective synthesis of electrophilic spirocyclopropanes in ionic liquids [J].
Calò, V ;
Nacci, A ;
Lopez, L ;
Lerario, VL .
TETRAHEDRON LETTERS, 2000, 41 (46) :8977-8980
[7]   Heck Reactions with Palladium Nanoparticles in Ionic Liquids: Coupling of Aryl Chlorides with Deactivated Olefins [J].
Calo, Vincenzo ;
Nacci, Angelo ;
Monopoli, Antonio ;
Cotugno, Pietro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (33) :6101-6103
[8]   Palladium-Nanoparticle-Catalysed Ullmann Reactions in Ionic Liquids with Aldehydes as the Reductants: Scope and Mechanism [J].
Calo, Vincenzo ;
Nacci, Angelo ;
Monopoli, Antonio ;
Cotugno, Pietro .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (05) :1272-1279
[9]  
Charette A.B., 2001, ORG REACT, V58, P1, DOI DOI 10.1002/0471264180.OR058.01
[10]   Recent advances in the total synthesis of cyclopropane-containing natural products [J].
Chen, David Y. -K. ;
Pouwer, Rebecca H. ;
Richard, Jean-Alexandre .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (13) :4631-4642
123