Insights into the general and efficient cross McMurry reactions between ketones

被引:139
作者
Duan, Xin-Fang [1 ]
Zeng, Jing [1 ]
Lu, Jia-Wei [1 ]
Zhang, Zhan-Bin [1 ]
机构
[1] Beijing Normal Univ, Dept Chem, Beijing 100875, Peoples R China
关键词
D O I
10.1021/jo061644d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The selective cross McMurry couplings of diaryl or aryl ketones with various substituted ketones were achieved in 53-94% isolated yields. It is believed that the strong affinity of the substituents to the low-valent titanium surface plays an important role in regards to moderating selectivity. Through the introduction of such substituents followed by their removal post McMurry coupling, structurally similar ketones can be effectively cross-coupled.
引用
收藏
页码:9873 / 9876
页数:4
相关论文
共 23 条
[1]  
ALBERTO S, 2000, Patent No. 608410
[2]   THE TOTAL SYNTHESIS OF CANNITHRENE-2 [J].
CASTEDO, L ;
SAA, JM ;
SUAU, R ;
TOJO, G .
TETRAHEDRON LETTERS, 1983, 24 (48) :5419-5420
[3]   Synthesis of (Z)-4-hydroxytamoxifen and (Z)-2-[4-[1-(p-hydroxyphenyl)-2-phenyl]-1-butenyl]phenoxyacetic acid [J].
Detsi, A ;
Koufaki, M ;
Calogeropoulou, T .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) :4608-4611
[4]   Total synthesis of archaeal 72-membered macrocyclic tetraether lipids [J].
Eguchi, T ;
Ibaragi, K ;
Kakinuma, K .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2689-2698
[5]   FIRST SYNTHESIS OF AN ARCHAEBACTERIAL 36-MEMBERED MACROCYCLIC DIETHER LIPID [J].
EGUCHI, T ;
TERACHI, T ;
KAKINUMA, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (02) :137-138
[6]   A new look at the McMurry reaction [J].
Ephritikhine, M .
CHEMICAL COMMUNICATIONS, 1998, (23) :2549-2554
[7]   New developments in the chemistry of low-valent titanium [J].
Furstner, A ;
Bogdanovic, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (21) :2442-2469
[8]   New highly stereoselective synthesis of (Z)-4-Hydroxytamoxifen and (Z)-4-hydroxytoremifene via McMurry reaction [J].
Gauthier, S ;
Mailhot, J ;
Labrie, F .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3890-3893
[9]  
JACKSON WP, 1998, Patent No. 9838166
[10]   CARBONYL COUPLING REACTIONS USING TRANSITION-METALS, LANTHANIDES, AND ACTINIDES [J].
KAHN, BE ;
RIEKE, RD .
CHEMICAL REVIEWS, 1988, 88 (05) :733-745