Pd(II)-bipyridine catalyzed conjugate addition of arylboronic acid to α,β-unsaturated carbonyl compounds

被引:139
作者
Lu, XY [1 ]
Lin, SH [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/jo051561h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A Pd(II)-catalyzed conjugate addition of arylboronic acid to alpha,beta-unsaturated ketones, aldehydes, esters, etc. in the presence of 2,2'-bipyridine was developed. A mechanism involving transmetalation, insertion of the carbon-carbon double bond into the C-Pd bond, and protonolysis of the resulting C-Pd bond is proposed. The reaction conditions are mild and the yield is high. The presence of 2,2'-bipyridine is crucial for the reaction to inhibit beta-hydride elimination.
引用
收藏
页码:9651 / 9653
页数:3
相关论文
共 34 条
[1]   PALLADIUM-CATALYZED CONJUGATE ADDITION TYPE REACTION OF (2-HYDROXYARYL)MERCURY CHLORIDES WITH ALPHA,BETA-UNSATURATED KETONES IN A 2-PHASE SYSTEM - A NEW SYNTHESIS OF 2-CHROMANOLS AND 2-CHROMENES [J].
CACCHI, S ;
MISITI, D ;
PALMIERI, G .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (15) :2995-2999
[2]   THE PALLADIUM-CATALYZED CONJUGATE ADDITION TYPE REACTION OF ARYLMERCURY COMPOUNDS WITH ALPHA,BETA-UNSATURATED KETONES IN A 2-PHASE SYSTEM [J].
CACCHI, S ;
MISITI, D ;
PALMIERI, G .
TETRAHEDRON, 1981, 37 (16) :2941-2946
[3]  
CACCHI S, 1979, TETRAHEDRON LETT, V20, P4591
[4]   Palladium(II)-catalyzed conjugate addition of aromatics to alpha,beta-unsaturated ketones and aldehydes with arylantimony compounds [J].
Cho, CS ;
Motofusa, S ;
Ohe, K ;
Uemura, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1996, 69 (08) :2341-2348
[5]   PALLADIUM(II)-CATALYZED HYDROARYLATION OF ALPHA,BETA-UNSATURATED ALDEHYDES AND KETONES WITH TRIARYLSTIBINES IN THE PRESENCE OF SILVER ACETATE [J].
CHO, CS ;
TANABE, K ;
UEMURA, S .
TETRAHEDRON LETTERS, 1994, 35 (08) :1275-1278
[6]   RHODIUM(I)-CATALYZED AND PALLADIUM(0)-CATALYZED CARBONYLATION OF TRIARYLBISMUTHINES WITH CARBON-MONOXIDE VIA A POSSIBLE OXIDATIVE ADDITION OF A CARBON BISMUTH BOND TO RHODIUM(I) AND PALLADIUM(0) [J].
CHO, CS ;
YOSHIMORI, Y ;
UEMURA, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (03) :950-957
[7]   A NEW CATALYTIC ACTIVITY OF ANTIMONY(III) CHLORIDE IN PALLADIUM(0)-CATALYZED CONJUGATE ADDITION OF AROMATICS TO ALPHA,BETA-UNSATURATED KETONES AND ALDEHYDES WITH SODIUM TETRAPHENYLBORATE AND ARYLBORONIC ACIDS [J].
CHO, CS ;
MOTOFUSA, S ;
OHE, K ;
UEMURA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) :883-888
[8]   Palladium-catalyzed conjugate addition of organosiloxanes to α,β-unsaturated carbonyl compounds and nitroalkenes [J].
Denmark, SE ;
Amishiro, N .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :6997-7003
[9]   Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions [J].
Hayashi, T ;
Yamasaki, K .
CHEMICAL REVIEWS, 2003, 103 (08) :2829-2844
[10]  
Jeffery T., 1996, ADV MET ORG, P153