Regioselective Cleavage of Unstrained C-C Bond and C-H Bond: Palladium-Copper Catalyzed Deacetophenonylative Arylation of Coumarin Derivatives

被引:7
作者
Sun, Manman [1 ]
Shen, Guodong [1 ]
Bao, Weiliang [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Peoples R China
关键词
C?C bond cleavage; copper; coumarins; palladium; 2-ARYLACETIC ACID-ESTERS; CARBON-CARBON BONDS; LEWIS-ACID; ACTIVATION; KETONES; ALKENES; CYCLOBUTANONES; ARYLMETHANOLS; CYCLOADDITION; ACETOACETATE;
D O I
10.1002/adsc.201200539
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A Ca?C beta bond activation of the carbonyl group in unstrained ketones catalyzed cooperatively by palladium and copper(II) with the departure of the acetophenone has been developed, and the subsequent coupling with a variety of aromatics via the formal C?H activation similar to the FriedelCrafts reaction affords the skeleton-reconstructed coumarin derivatives with high regioselectivity.
引用
收藏
页码:3468 / 3474
页数:7
相关论文
共 58 条
[1]  
[Anonymous], 2010, ANGEW CHEM INT ED, V49, P1820
[2]  
[Anonymous], 2009, ANGEW CHEM INT ED, V48, P2452
[3]  
[Anonymous], 2009, ANGEW CHEM, V121, P2488
[4]  
[Anonymous], 2007, ANGEW CHEM INT ED, V46, P2643
[5]  
[Anonymous], 1999, ANGEW CHEM INT ED, V38, P870
[6]  
[Anonymous], 2009, ANGEW CHEM INT ED, V48, P2460
[7]  
[Anonymous], 1997, ANGEW CHEM INT ED EN, V36, P2352
[8]   Selective, catalytic carbon-carbon bond activation and functionalization promoted by late transition metal catalysts [J].
Bart, SC ;
Chirik, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (04) :886-887
[9]   The Aromatic Carbon-Carbon ipso-Substitution Reaction [J].
Bonesi, Sergio M. ;
Fagnoni, Maurizio .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (46) :13572-13589
[10]   Ru3(CO)12-catalyzed decarbonylative cleavage of a C-C bond of alkyl phenyl ketones [J].
Chatani, N ;
Ie, Y ;
Kakiuchi, F ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (37) :8645-8646