Copper-Mediated Fluoroalkylation Reactions with Iododifluoroacetamides: Controlling the Selectivity among Cross-Coupling, Intramolecular Cyclization, and Homocoupling Reactions

CORC > 上海有机化学研究所 > 中国科学院上海有机化学研究所 > 中科院有机氟化学重点实验室

	Copper-Mediated Fluoroalkylation Reactions with Iododifluoroacetamides: Controlling the Selectivity among Cross-Coupling, Intramolecular Cyclization, and Homocoupling Reactions
	Zhu JM(朱杰明) ; Zhang W(张伟) ; Zhang LJ(张来俊) ; Liu J(刘俊) ; Zheng J(郑吉) ; Hu JB(胡金波)
刊名	J. Org. Chem.
	2010
卷号	75 期号:16 页码:5505-5512
ISSN号	0022-3263
其他题名	单质铜参与的利用一碘二氟乙酰胺进行氟烷基化反应: 控制交叉偶联、分子内成环、自偶联反应之间的选择性
通讯作者	胡金波
英文摘要	Cu-mediated fluoroalkylation reactions with iododifluoroacetamides I have been systematically investigated. It was found that three types of reactions may coexist in Cu-mediated reactions between iododifluoroacetamides and aryl/alkenyl iodides: cross-coupling, intramolecular cyclization, and homocoupling reactions. The selectivity among these three types of reactions could be controlled by tuning the substituents on the nitrogen atom of iododifluoroacetamides, and/or by removing the cross-coupling reaction partner (aryl/alkenyl halides). The general rule is as follows: (a) in the presence of proper aryl/alkenyl iodides, the cross-coupling products 2 (or 6) are generally formed as the major products; (b) in the absence of aryl/alkenyl iodides, and when R-1 = alkyl and R-2 = aryl groups, or when R-1 = R-2 = aryl groups, the intramolecular cyclization products 3 can be formed predominantly; and (c) in the absence of aryl/alkenyl iodides, and when R-1 = R-2 = alkyl groups, or when R-1 = H and R-2 = alkyl, aryl groups, the homocoupling products 4 can be formed dominantly. Our experimental results also indicate that in many cases when cross-coupling, homocoupling, and intramolecular cyclization reactions coexist in the Cu-mediated reaction system, the reactivity decreases in the following order: cross-coupling > intramolecular cyclization > homocoupling.
学科主题	氟化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1021/jo1005262
语种	英语
WOS记录号	WOS:000280798900009
公开日期	2013-03-11
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/24069]
专题	上海有机化学研究所_中科院有机氟化学重点实验室
推荐引用方式 GB/T 7714	Zhu JM,Zhang W,Zhang LJ,et al. Copper-Mediated Fluoroalkylation Reactions with Iododifluoroacetamides: Controlling the Selectivity among Cross-Coupling, Intramolecular Cyclization, and Homocoupling Reactions[J]. J. Org. Chem.,2010,75(16):5505-5512.
APA	朱杰明,张伟,张来俊,刘俊,郑吉,&胡金波.(2010).Copper-Mediated Fluoroalkylation Reactions with Iododifluoroacetamides: Controlling the Selectivity among Cross-Coupling, Intramolecular Cyclization, and Homocoupling Reactions.J. Org. Chem.,75(16),5505-5512.
MLA	朱杰明,et al."Copper-Mediated Fluoroalkylation Reactions with Iododifluoroacetamides: Controlling the Selectivity among Cross-Coupling, Intramolecular Cyclization, and Homocoupling Reactions".J. Org. Chem. 75.16(2010):5505-5512.