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题名: Iron-Mediated Oxidative C-H Alkylation of S,S-Functionalized Internal Olefins via C(sp(2))-H/C(sp(3))-H Cross-Coupling
作者: Wang, Quannan1, 2;  Lou, Jiang1, 2;  Wu, Ping1, 2;  Wu, Kaikai1;  Yu, Zhengkun1, 3
关键词: alkylation ;  C-H functionalization ;  C-H/C-H cross-coupling ;  internal olefins ;  iron
刊名: ADVANCED SYNTHESIS & CATALYSIS
发表日期: 2017-09-04
DOI: 10.1002/adsc.201700654
卷: 359, 期:17, 页:2981-2998
收录类别: SCI
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Applied ;  Chemistry, Organic
研究领域[WOS]: Chemistry
英文摘要: Mediated by a catalytic amount of FeCl3, the C-H alkylation of S, S-functionalized internal ole-fins, i.e., alpha-oxo ketene dithioacetals and their analogues, was efficiently achieved using simple ethers and toluene derivatives as the coupling partners, ditert-butyl peroxide (DTBP) as the oxidant, and DABCO center dot 6H(2)O as the additive. The alkylthio functionality is essential for the internal olefinic C-H bond to undergo such an alkylation with the O-adjacent C(sp(3))-H bonds of the ethers and the benzylic C-H bonds of the toluene derivatives, respectively. Tetrasubstituted olefins were thus synthesized and further transformed to highly substituted pyrazoles and isoxazoles. The strategy to activate an internal olefinic C-H bond by polarizing its parent olefinic C=C bond with both the dialkylthio group and an electron-withdrawing functionality was investigated. The mechanistic studies suggest a radical pathway for the C(sp(2))-H/C(sp(3))-H cross-coupling reactions. The present protocol provides a convenient route to tetrasubstituted olefins.
关键词[WOS]: OXO KETENE DITHIOACETALS ;  EFFICIENT SYNTHESIS ;  BOND ACTIVATION ;  STEREOSELECTIVE-SYNTHESIS ;  MULTISUBSTITUTED OLEFINS ;  DIRECT FUNCTIONALIZATION ;  DIRECT ALKENYLATION ;  ORGANIC-SYNTHESIS ;  FACILE SYNTHESIS ;  BUILDING-BLOCKS
语种: 英语
WOS记录号: WOS:000408941200012
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/149868
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Chinese Acad Sci, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Liaoning, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
3.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R China

Recommended Citation:
Wang, Quannan,Lou, Jiang,Wu, Ping,et al. Iron-Mediated Oxidative C-H Alkylation of S,S-Functionalized Internal Olefins via C(sp(2))-H/C(sp(3))-H Cross-Coupling[J]. ADVANCED SYNTHESIS & CATALYSIS,2017,359(17):2981-2998.
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