LICP OpenIR  > 羰基合成与选择氧化国家重点实验室(OSSO)
Markovnikov-Selective Radical Addition of S-Nucleophiles to Terminal Alkynes through a Photoredox Process
DepartmentOSSO国家重点实验室
Wang, Huamin1; Lu, Qingquan1; Chiang, Chien-Wei1; Luo, Yi1; Zhou, Jiufu1; Wang, Guangyu1; Lei AW(雷爱文)1,2; Lei AW(雷爱文)
2017
Source PublicationAngewandte Chemie International Edition
ISSN1433-7851
Volume56Issue:2Pages:595-599
Abstract

Direct radical additions to terminal alkynes have been widely employed in organic synthesis, providing credible access to the anti-Markovnikov products. Because of the Kharasch effect, regioselective control for the formation of Markovnikov products still remains a great challenge. Herein, we develop a transition-metal-free, visible light-mediated radical addition of S-nucleophiles to terminal alkynes, furnishing a wide array of [alpha]-substituted vinyl sulfones with exclusive Markovnikov regioselectivity. Mechanistic investigations demonstrated that radical/radical cross-coupling might be the key step in this transformation. This radical Markovnikov addition protocol also provides an opportunity to facilitate the synthesis of other valuable [alpha]-substituted vinyl compounds.

KeywordMarkovnikov Selectivity Photoredox Catalysis Radical Addition Radical Cross Coupling Transition-metal-free Synthesis
Subject Area物理化学与绿色催化
DOI10.1002/anie.201610000
Funding Organizationthe National Natural Science Foundation of China (21390400;21520102003; 21272180;21302148);the Hubei Province Natural Science Foundation of China (2013CFA081);the Research Fund for the Doctoral Program of Higher Education of China (20120141130002);the Ministry of Science and Technology of China (2012YQ120060);the Program of Introducing Talents of Discipline to Universities of China (111 Program)
Indexed BySCI
If11.994
Language英语
compositor第二作者单位
Citation statistics
Cited Times:107[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.licp.cn/handle/362003/21519
Collection羰基合成与选择氧化国家重点实验室(OSSO)
Corresponding AuthorLei AW(雷爱文)
Affiliation1.Wuhan Univ, IAS, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China
2.Chinese Acad Sci, Lanzhou Inst Chem Phys, Lanzhou 730000, Peoples R China
Recommended Citation
GB/T 7714
Wang, Huamin,Lu, Qingquan,Chiang, Chien-Wei,et al. Markovnikov-Selective Radical Addition of S-Nucleophiles to Terminal Alkynes through a Photoredox Process[J]. Angewandte Chemie International Edition,2017,56(2):595-599.
APA Wang, Huamin.,Lu, Qingquan.,Chiang, Chien-Wei.,Luo, Yi.,Zhou, Jiufu.,...&雷爱文.(2017).Markovnikov-Selective Radical Addition of S-Nucleophiles to Terminal Alkynes through a Photoredox Process.Angewandte Chemie International Edition,56(2),595-599.
MLA Wang, Huamin,et al."Markovnikov-Selective Radical Addition of S-Nucleophiles to Terminal Alkynes through a Photoredox Process".Angewandte Chemie International Edition 56.2(2017):595-599.
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