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Iron-Mediated Oxidative C-H Alkylation of S,S-Functionalized Internal Olefins via C(sp(2))-H/C(sp(3))-H Cross-Coupling
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
2017-09-04
DOI10.1002/adsc.201700654
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
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
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.
语种英语
WOS记录号WOS:000408941200012
引用统计
文献类型期刊论文
条目标识符http://cas-ir.dicp.ac.cn/handle/321008/149968
专题中国科学院大连化学物理研究所
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
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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.
APA Wang, Quannan,Lou, Jiang,Wu, Ping,Wu, Kaikai,&Yu, Zhengkun.(2017).Iron-Mediated Oxidative C-H Alkylation of S,S-Functionalized Internal Olefins via C(sp(2))-H/C(sp(3))-H Cross-Coupling.ADVANCED SYNTHESIS & CATALYSIS,359(17),2981-2998.
MLA Wang, Quannan,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".ADVANCED SYNTHESIS & CATALYSIS 359.17(2017):2981-2998.
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