Palladium-Catalyzed Cycloisomerizations of (Z)-1-Iodo-1,6-dienes: Iodine Atom Transfer and Mechanistic Insight to Alkyl Iodide Reductive Elimination

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	Palladium-Catalyzed Cycloisomerizations of (Z)-1-Iodo-1,6-dienes: Iodine Atom Transfer and Mechanistic Insight to Alkyl Iodide Reductive Elimination
	Liu, H ; Li, CL ; Qiu, D ; Tong, XF
刊名	JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
	2011
卷号	133 期号:16 页码:6187
关键词	CROSS-COUPLING REACTIONS ARYLPALLADIUM(II) HALIDE-COMPLEXES RADICAL CYCLIZATION REACTIONS ARYL HALIDES BOND FORMATION CARBON-MONOXIDE OXIDATIVE ADDITION HALOGEN EXCHANGE STEREOSELECTIVE-SYNTHESIS HECK REACTION
ISSN号	0002-7863
通讯作者	Qiu, D (reprint author), Chinese Acad Sci ICCAS, Beijing Natl Lab Mol Sci, State Key Lab Polymer Phys & Chem, Inst Chem, Beijing 100190, Peoples R China.
中文摘要	A palladium-catalyzed iodine atom transfer cycloisomerization of (Z)-1-iodo-1,6-diene has been developed, which provides a facile method to construct six-memebered heterocycles bearing an alkyl iodide group. The ligand screening shows that both the type and the quantity of ligand impose significant influences on this transformation, and the combination of 30 mol % 1,1'-bis(diphenylphosphino)ferrocene (DPPF) and 10 mol % Pd(OAc)(2) is the optimal choice. The catalytic cycle, consisting of oxidative addition of Pd(0) to vinyl iodide, intramolecular alkene insertion, and alkyl iodide reductive elimination, has been proposed and eventually supported by convincing evidence from a series of control experiments. More importantly, these control experiments disclose some features of the event of alkyl iodide reductive elimination: (1) this reductive elimination is proved to be a stereospecific process; and (2) both alkyl iodide oxidative addition and reductive elimination are not effected by a TEMPO additive. Besides its ability to undergo oxidative addition, the catalyst (palladium + DPPF) could also promote a radical transfer process. The findings described in this paper will be helpful for further development of the metal-catalyzed formation of a carbon-halide bond.
收录类别	SCI
资助信息	Shanghai Municipal Committee of Science and Technology [09ZR1408500]; Fundamental Research Funds for the Central Universities
语种	英语
公开日期	2013-09-24
内容类型	期刊论文
源URL	[http://ir.iphy.ac.cn/handle/311004/50561]
专题	物理研究所_物理所公开发表论文_物理所公开发表论文_期刊论文
推荐引用方式 GB/T 7714	Liu, H,Li, CL,Qiu, D,et al. Palladium-Catalyzed Cycloisomerizations of (Z)-1-Iodo-1,6-dienes: Iodine Atom Transfer and Mechanistic Insight to Alkyl Iodide Reductive Elimination[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2011,133(16):6187.
APA	Liu, H,Li, CL,Qiu, D,&Tong, XF.(2011).Palladium-Catalyzed Cycloisomerizations of (Z)-1-Iodo-1,6-dienes: Iodine Atom Transfer and Mechanistic Insight to Alkyl Iodide Reductive Elimination.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,133(16),6187.
MLA	Liu, H,et al."Palladium-Catalyzed Cycloisomerizations of (Z)-1-Iodo-1,6-dienes: Iodine Atom Transfer and Mechanistic Insight to Alkyl Iodide Reductive Elimination".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 133.16(2011):6187.