Palladium-catalyzed cross-coupling reactions in one-pot multicatalytic processes

被引:78
作者
Lebel, Helene [1 ]
Ladjel, Chehla [1 ]
Brethous, Lise [1 ]
机构
[1] Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
关键词
D O I
10.1021/ja0733235
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Palladium-catalyzed cross-coupling reactions have been investigated in multicatalytic processes to synthesize disubstituted alkenes and alkanes from carbonyl derivatives. The use of copper-catalyzed methylenation reactions is the key starting reaction to produce terminal alkenes which are not isolated, but submitted to further structure elongation. Not only is the isolation of the alkene intermediate unnecessary, but also the copper catalyst is a beneficial cocatalyst in the palladium-catalyzed cross-coupling reactions. The desired products are thus typically obtained in higher yields using this one-pot approach. We have used these processes to synthesize hydroxylated (E)-stilbenoids, which are known chemopreventive and chemotherapeutic agents, odorant-substituted indanes, and non-natural amino acids, such as homophenylalanine.
引用
收藏
页码:13321 / 13326
页数:6
相关论文
共 118 条
[1]   One-pot 2-aryl/vinylindole synthesis consisting of a ruthenium-catalyzed hydroamination and a palladium-catalyzed Heck reaction using 2-chloroaniline [J].
Ackermann, Lutz ;
Althammer, Andreas .
SYNLETT, 2006, (18) :3125-3129
[2]   Stilbene derivatives from Cissus quadrangularis [J].
Adesanya, SA ;
Nia, R ;
Martin, MT ;
Boukamcha, N ;
Montagnac, A ;
Païs, M .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (12) :1694-1695
[3]   Two birds with one metallic stone: Single-pot catalysis of fundamentally different transformations [J].
Ajamian, A ;
Gleason, JL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3754-3760
[4]   CROSS-COUPLING REACTION OF CHLOROPYRAZINES WITH ETHYLENES [J].
AKITA, Y ;
NOGUCHI, T ;
SUGIMOTO, M ;
OHTA, A .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (05) :1481-1485
[5]  
Alphonse FA, 2002, SYNLETT, P447
[6]  
[Anonymous], CHEMTRACTS
[7]   A highly stereospecific and efficient synthesis of homopentafluorophenylalanine [J].
Babu, IR ;
Hamill, EK ;
Kumar, K .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) :5468-5470
[8]   First total synthesis of the 4a-methyltetrahydrofluorene diterpenoids (±)-dichroanal B and (±)-dichroanone [J].
Banerjee, M ;
Mukhopadhyay, R ;
Achari, B ;
Banerjee, AK .
ORGANIC LETTERS, 2003, 5 (21) :3931-3933
[9]   Copper in cross-coupling reactions - The post-Ullmann chemistry [J].
Beletskaya, IP ;
Cheprakov, AV .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364
[10]   Controlled mono and double Heck reactions in water catalyzed by an oxime-derived palladacycle [J].
Botella, L ;
Nájera, C .
TETRAHEDRON LETTERS, 2004, 45 (09) :1833-1836