Catalytic conjugate addition of allyl groups to styryl-activated enones

被引:89
作者
Sieber, Joshua D.
Liu, Shubin
Morken, James P. [1 ]
机构
[1] Boston Coll, Dept Chem, Merkert Chem Ctr, Chestnut Hill, MA 02467 USA
[2] Univ N Carolina, Informat Technol Serv, Div Res Comp, Chapel Hill, NC 27599 USA
关键词
D O I
10.1021/ja067878w
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Conjugate addition of pinacolato(allyl)boron to benzylidenealkylidene ketones is remarkably facile when catalyzed by Ni(0) and Pd(0) complexes. Simple enones are inert to the reaction conditions, suggesting a significant activating effect by the auxiliary benzylidene unit. A comparison of different catalysts and substrates is provided, as is a mechanistic rationale, and an example of asymmetric catalysis.
引用
收藏
页码:2214 / +
页数:3
相关论文
共 47 条
[1]  
Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221
[2]   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
[3]   Nickel(0)-catalyzed asymmetric cross-coupling reactions of allylic compounds with arylboronic acids [J].
Chung, KG ;
Miyake, Y ;
Uemura, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (01) :15-18
[4]   P-N bond formation as a route to highly electron rich phosphine ligands [J].
Clarke, ML ;
Cole-Hamilton, DJ ;
Slawin, AMZ ;
Woollins, JD .
CHEMICAL COMMUNICATIONS, 2000, (20) :2065-2066
[5]   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
[6]  
Feringo BL, 2002, MODERN ORGANOCOPPER CHEMISTRY, P224, DOI 10.1002/3527600086.ch7
[7]   Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts [J].
Garber, SB ;
Kingsbury, JS ;
Gray, BL ;
Hoveyda, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8168-8179
[8]   Palladium-catalyzed enantioselective conjugate addition of arylboronic acids [J].
Gini, F ;
Hessen, B ;
Minnaard, AJ .
ORGANIC LETTERS, 2005, 7 (23) :5309-5312
[9]  
Gottlich R, 1997, SYNLETT, P971
[10]   NICKEL-CATALYZED, CHLOROTRIALKYLSILANE-ASSISTED CONJUGATE ADDITION OF ALKENYLTRIBUTYLTIN REAGENTS TO ALPHA,BETA-UNSATURATED ALDEHYDES - EVIDENCE FOR A [1-((TRIALKYLSILYL)OXY)ALLYL]NICKEL(II) MECHANISM [J].
GRISSO, BA ;
JOHNSON, JR ;
MACKENZIE, PB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5160-5165