One-Pot Access to Cinnamates via Direct Oxidative C-H Transformation of Allylarenes

被引:10
作者
Chang, Meng-Yang [1 ]
Lin, Shin-Ying [1 ]
Chan, Chieh-Kai [1 ]
机构
[1] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 807, Taiwan
关键词
allylarenes; C-H esterification; cinnamates; ALLYLIC OXIDATION; BOND FUNCTIONALIZATION; DDQ; AMINATION; CYCLIZATION; ACTIVATION; ALCOHOLS; ALKENES; ESTERS; CINNAMALDEHYDES;
D O I
10.1055/s-0032-1318146
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly selective combination of ruthenium complex and oxidant, which catalyzes the oxidative C-H esterification of allylarenes to the corresponding bis-(E)-cinnamates and (E)-cinnamates, is described. The one-pot route was carried out by olefinic migration of allylarenes with RuCl2(PPh3)(3) and DDQ-mediated allylic oxidation of the resulting internal alkenes with various alcohols in good yields.
引用
收藏
页码:487 / 490
页数:4
相关论文
共 51 条
[1]   Novel and highly selective conversion of alcohols and thiols to alkyl nitrites with triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/Bu4NNO2 system [J].
Akhlaghinia, B ;
Pourali, AR .
SYNTHESIS-STUTTGART, 2004, (11) :1747-1749
[2]   Synthesis of 2-arylbenzothiazoles by DDQ-promoted cyclization of thioformanilides; A solution-phase strategy for library synthesis [J].
Bose, D. Sublias ;
Idrees, Mohd. ;
Srikanth, Bingi .
SYNTHESIS-STUTTGART, 2007, (06) :819-823
[3]   Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles [J].
Campos, Kevin R. .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1069-1084
[4]   Synthesis of polyphenyls [J].
Chang, Meng-Yang ;
Lee, Tein-Wei ;
Lin, Shin-Ying .
TETRAHEDRON, 2013, 69 (01) :228-234
[5]   SYNTHESIS OF SUBSTITUTED DIHYDROBENZOFURANS AND BIS-DIHYDROBENZOFURANS [J].
Chang, Meng-Yang ;
Lee, Tein-Wei ;
Wu, Ming-Hao .
HETEROCYCLES, 2012, 85 (07) :1607-+
[6]   Polyphosphoric Acid Promoted Synthesis of 10,11-Dihydrobenzo[j]fluoranthen-12-one [J].
Chang, Meng-Yang ;
Lee, Tein-Wei ;
Wu, Ming-Hao .
ORGANIC LETTERS, 2012, 14 (09) :2198-2201
[7]   Facile Synthesis of (E)-Alkenyl Aldehydes from Allyl Arenes or Alkenes via Pd(II)-Catalyzed Direct Oxygenation of Allylic C-H Bond [J].
Chen, Huoji ;
Jiang, Huanfeng ;
Cai, Congbi ;
Dong, Jia ;
Fu, Wei .
ORGANIC LETTERS, 2011, 13 (05) :992-994
[8]   A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis [J].
Chen, Mark S. ;
White, M. Christina .
SCIENCE, 2007, 318 (5851) :783-787
[9]   A sulfoxide-promoted, catalytic method for the regioselective synthesis of allylic acetates from monosubstituted olefins via C-H oxidation [J].
Chen, MS ;
White, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (05) :1346-1347
[10]   Highly efficient metal-free cross-coupling by C-H activation between allylic and active methylenic compounds promoted by DDQ [J].
Cheng, Dongping ;
Bao, Weiliang .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (09) :1263-1266