Iron-Mediated Oxidative C-H Alkylation of S,S-Functionalized Internal Olefins via C(sp(2))-H/C(sp(3))-H Cross-Coupling
文献类型：期刊论文
| 作者 | Wang, Quannan2,3; Lou, Jiang2,3; Wu, Ping2,3; Wu, Kaikai2; Yu, Zhengkun1,2 |
| 刊名 | ADVANCED SYNTHESIS & CATALYSIS
 |
| 出版日期 | 2017-09-04 |
| 卷号 | 359期号:17页码:2981-2998 |
| 关键词 | alkylation C-H functionalization C-H/C-H cross-coupling internal olefins iron |
| 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. |
| 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 |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000408941200012 |
| 源URL | [http://cas-ir.dicp.ac.cn/handle/321008/149868]  |
| 专题 | 大连化学物理研究所_中国科学院大连化学物理研究所 |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R China 2.Chinese Acad Sci, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Liaoning, Peoples R China 3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China |
| 推荐引用方式 GB/T 7714 | 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. |
入库方式： OAI收割
来源：大连化学物理研究所
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