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Conjugated Diene-Assisted Allylic C-H Bond Activation: Cationic Rh(I)-Catalyzed Syntheses of Polysubstituted Tetrahydropyrroles, Tetrahydrofurans, and Cyclopentanes from Ene-2-Dienes
Li, Qian; Yu, Zhi-Xiang1
2010-04-07
Source PublicationJOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN0002-7863
Volume132Issue:13Pages:4542-+
AbstractC-H activation followed by addition to alkenes is challenging in the current C-H activation/functionalization field. We report herein an unprecedented diene-assisted transition-metal-catalyzed activation of allylic C-H bonds and their subsequent insertion into the alkene moieties of conjugated dienes. This novel C-H activation/alkene insertion reaction provides an efficient way to synthesize polysubstituted tetrahydropyrroles, tetrahydrofurans, and cyclopentanes with quaternary carbon centers. Preliminary mechanistic studies using D-labeling experiments have revealed that allylic C-H activation and alkene insertion are reversible steps, whereas the reductive elimination step, which is the final and the rate-determining step of the catalytic cycle, is irreversible.
DOI10.1021/ja100409b
Indexed BySCI ; IC ; CCR
Language英语
WOS IDWOS:000276553600020
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:43[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/70296
Collection中国科学院化学研究所
Corresponding AuthorYu, Zhi-Xiang
Affiliation1.Peking Univ, BNLMS, Beijing 100871, Peoples R China
2.Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Coll Chem & Mol Engn, Beijing 100871, Peoples R China
Recommended Citation
GB/T 7714
Li, Qian,Yu, Zhi-Xiang. Conjugated Diene-Assisted Allylic C-H Bond Activation: Cationic Rh(I)-Catalyzed Syntheses of Polysubstituted Tetrahydropyrroles, Tetrahydrofurans, and Cyclopentanes from Ene-2-Dienes[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2010,132(13):4542-+.
APA Li, Qian,&Yu, Zhi-Xiang.(2010).Conjugated Diene-Assisted Allylic C-H Bond Activation: Cationic Rh(I)-Catalyzed Syntheses of Polysubstituted Tetrahydropyrroles, Tetrahydrofurans, and Cyclopentanes from Ene-2-Dienes.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,132(13),4542-+.
MLA Li, Qian,et al."Conjugated Diene-Assisted Allylic C-H Bond Activation: Cationic Rh(I)-Catalyzed Syntheses of Polysubstituted Tetrahydropyrroles, Tetrahydrofurans, and Cyclopentanes from Ene-2-Dienes".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 132.13(2010):4542-+.
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