An Efficient Method for the Selective Iodination of α,β-Unsaturated Ketones

被引:34
作者
Wang, Zihua [1 ]
Yin, Guodong [1 ]
Qin, Jing [1 ]
Gao, Meng [1 ]
Cao, Liping [1 ]
Wu, Anxin [1 ]
机构
[1] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China
来源
SYNTHESIS-STUTTGART | 2008年 / 22期
基金
中国国家自然科学基金;
关键词
iodination; alpha; beta-unsaturated ketones; beta-unsaturated alpha '-iodo ketones; self-sorting;
D O I
10.1055/s-0028-1083200
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient approach to alpha,beta-unsaturated alpha'-iodo ketones directly from alpha,beta-unsaturated ketones by selective iodination at the alpha'-position, without effect on the double bond and the activated benzene ring, in the presence of copper(II) oxide/iodine is described. The present method has the advantages of high yields, short reaction times, inexpensive reagents, mild reaction conditions, ease of manipulation, and the formation of cleaner products.
引用
收藏
页码:3675 / 3681
页数:7
相关论文
共 46 条
[41]   STEREOCHEMICAL BEHAVIOR OF INTERMEDIARY COMPOUNDS IN THE AMINE-CATALYZED KNOEVENAGEL REACTION [J].
TANIKAGA, R ;
KONYA, N ;
HAMAMURA, K ;
KAJI, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (09) :3211-3216
[42]   Differentiation of nonconventional "Carbanions"- The total synthesis of nemorosone and clusianone [J].
Tsukano, Chihiro ;
Siegel, Dionicio R. ;
Danishefsky, Samuel J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8840-8844
[43]   Novel alpha-iodination of functionalized ketones with iodine mediated by bis(tetra-n-butylammonium) peroxydisulfate [J].
Whang, JP ;
Yang, SG ;
Kim, YH .
CHEMICAL COMMUNICATIONS, 1997, (15) :1355-1356
[44]   A new facile approach to the synthesis of 3-methylthio-substituted furans, pyrroles, thiophenes, and related derivatives [J].
Yin, Guodong ;
Wang, Zihua ;
Chen, Aihua ;
Gao, Meng ;
Wu, Anxin ;
Pan, Yuanjiang .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09) :3377-3383
[45]   Highly efficient and clean method for direct α-iodination of aromatic ketones [J].
Yin, Guodong ;
Gao, Meng ;
She, Nengfang ;
Hu, Shengli ;
Wu, Anxin ;
Pan, Yuanjiang .
SYNTHESIS-STUTTGART, 2007, 20 (20) :3113-3116
[46]   Efficient C-C double-bond formation reaction via a new synthetic strategy: A self-sorting tandem reaction [J].
Yin, Guodong ;
Zhou, Baohan ;
Meng, Xianggao ;
Wu, Anxin ;
Pan, Yuanjiang .
ORGANIC LETTERS, 2006, 8 (11) :2245-2248