Palladium-Catalyzed Benzylation of Carboxylic Acids with Toluene via Benzylic C-H Activation

被引:97
作者
Liu, Hongqiang [1 ]
Shi, Guangfa [1 ]
Pan, Shulei [1 ]
Jiang, Yuyu [1 ]
Zhang, Yanghui [1 ]
机构
[1] Tongji Univ, Dept Chem, Shanghai 200092, Peoples R China
关键词
BOND FORMATION; CARBON-HYDROGEN; OXIDATIVE FUNCTIONALIZATION; COUPLING REACTIONS; ACETOXYLATION; ESTERIFICATION; ALKYLBENZENES; LACTONIZATION; PHI(OAC)(2); COMPLEXES;
D O I
10.1021/ol401687f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct benzylation of carboxylic acids with toluene has been developed via palladium-catalyzed C-H acyloxylation under 1 atm of oxygen. This reaction demonstrates good functional group tolerance and high yields, providing a facile, atom-economic, and efficient method for the synthesis of benzyl esters.
引用
收藏
页码:4098 / 4101
页数:4
相关论文
共 52 条
[1]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[2]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[3]   Propolis Specimens from Different Locations of Central Italy: Chemical Profiling and Gas Chromatography-Mass Spectrometry (GC-MS) Quantitative Analysis of the Allergenic Esters Benzyl Cinnamate and Benzyl Salicylate [J].
Aliboni, Andrea ;
D'Andrea, Armando ;
Massanisso, Paolo .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2011, 59 (01) :282-288
[4]   Transition-Metal-Catalyzed Synthesis of Hydroxylated Arenes [J].
Alonso, Diego A. ;
Najera, Carmen ;
Pastor, Isidro M. ;
Yus, Miguel .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (18) :5274-5284
[5]   Benzylic-acetoxylation of alkylbenzenes with PhI(OAc)2 in the presence of catalytic amounts of TsNH2 and I2 [J].
Baba, Haruka ;
Moriyama, Katsuhiko ;
Togo, Hideo .
TETRAHEDRON LETTERS, 2011, 52 (33) :4303-4307
[6]  
BRYANT DR, 1968, TETRAHEDRON LETT, P3371
[7]   A PALLADIUM-CATALYZED SYNTHESIS OF BENZYL ESTERS FROM METHYLBENZENES [J].
BRYANT, DR ;
MCKEON, JE ;
REAM, BC .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (11) :4123-&
[8]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115
[9]   Pd(II)-Catalyzed Enantioselective C-H Activation/C-O Bond Formation: Synthesis of Chiral Benzofuranones [J].
Cheng, Xiu-Fen ;
Li, Yan ;
Su, Yi-Ming ;
Yin, Feng ;
Wang, Jian-Yong ;
Sheng, Jie ;
Vora, Harit U. ;
Wang, Xi-Sheng ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (04) :1236-1239
[10]   Palladium-Catalyzed Direct and Regioselective C-H Bond Functionalization/Oxidative Acetoxylation of Indoles [J].
Choy, Pui Ying ;
Lau, Chak Po ;
Kwong, Fuk Yee .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (01) :80-84