Unusual cleavage of the enolsilane C-O bond: Transformation of 2-silyloxy-1,3-dienes into 1,3-dienyl-2-zirconium compounds and their cross-coupling reactions

被引：0
作者：
Ganchegui, B
Bertus, P
Szymoniak, J [1 ]
机构：
[1] CNRS, F-51687 Reims 2, France
[2] Univ Reims, F-51687 Reims, France
来源：
SYNLETT | 2001年 / 01期
关键词：
silyloxydienes; zirconium; dienylzirconocenes; cross-coupling;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Aryl enolsilanes and 2-silyloxy-1,3-dienes react with zirconocene to give alkenylzirconium, and novel 1-methylene-2-propenylzirconium compounds which can be used as 2-dienylation reagents. Thus, one-pot coupling of 4-phenyl-1,3-butadienyl-2-zirconocene (2d) with a range of electrophiles including aryl, alkynyl, allyl halides, bromine, iodine and a Michael acceptor occurs regioselectively at the C-2 position in the presence of Pd or Cu catalysts.
引用
收藏
页码：123 / 125
页数：3
相关论文
共 30 条
[1]  
[Anonymous], CHEM SOC REV
[2]   THERMAL AND CATALYZED DIELS-ALDER REACTIONS WITH CHIRAL 2-SUBSTITUTED-1,3-DIENES - CONFORMATIONAL MODELS FOR DIASTEREOFACIAL SELECTIVITY [J].
BLOCH, R ;
CHAPTALGRADOZ, N .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) :4162-4169
[3]  
BRANDSMA L, 1998, APPL TRANSITION META, P42
[4]  
Colvin E. W., 1985, SILICON ORGANIC SYNT
[5]  
Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222
[6]   TRANSITION-METAL DIENYLS IN ORGANIC-SYNTHESIS - A CONVENIENT PREPARATION OF SIGMA-BONDED TIN AND ZIRCONIUM DIENYLS [J].
FRYZUK, MD ;
BATES, GS ;
STONE, C .
TETRAHEDRON LETTERS, 1986, 27 (14) :1537-1540
[7]   Vinylic C-F bond activation with low-valent zirconocene: the generation and cross-coupling reactions of 1-fluorovinylzirconocene [J].
Fujiwara, M ;
Ichikawa, J ;
Okauchi, T ;
Minami, T .
TETRAHEDRON LETTERS, 1999, 40 (40) :7261-7265
[8]   New transformations from a 3-silyloxy 2-aza-1,3-diene: Consecutive Zr-mediated retro-Brook rearrangement and reactions with electrophiles [J].
Gandon, V ;
Bertus, P ;
Szymoniak, J .
TETRAHEDRON, 2000, 56 (26) :4467-4472
[9]   Reaction of 3-trimethylsilyloxy-2-aza-1,3-dienes with zirconocene: a transition metal promoted retro-Brook rearrangement [J].
Gandon, V ;
Bertus, P ;
Szymoniak, J .
TETRAHEDRON LETTERS, 2000, 41 (17) :3053-3056
[10]   Highly substituted enyne formation by coupling reaction of alkenylzirconium compounds with alkynyl halides [J].
Hara, R ;
Liu, YH ;
Sun, WH ;
Takahashi, T .
TETRAHEDRON LETTERS, 1997, 38 (23) :4103-4106
123