gem-Difluoroolefination of Diazo Compounds with TMSCF3 or TMSCF2Br: Transition-Metal-Free Cross-Coupling of Two Carbene Precursors
文献类型：期刊论文
| 作者 | Hu MY(胡明友)1; Ni CF(倪传法)1; Li LC(李铃春)1; Han YX(韩永新)1; Hu JB(胡金波)1 |
| 刊名 | J. Am. Chem. Soc.
 |
| 出版日期 | 2015 |
| 卷号 | 137期号:45页码:14496-14501 |
| 其他题名 | 以二氟卡宾试剂TMSCF3或TMSCF2Br对重氮化合物的偕二氟烯化反应: 两种不同卡宾前体在无过渡金属条件下的交叉偶联 |
| 通讯作者 | 胡金波 |
| 英文摘要 | A new olefination protocol for transition-metal-free cross-coupling of two carbene fragments arising from two different sources, namely, a nonfluorinated carbene fragment resulting from a diazo compound and a difluorocarbene fragment derived from Ruppert-Prakash reagent (TMSCF3) or TMSCF2Br, has been developed. This gem-difluoroolefination proceeds through the direct nucleophilic addition of diazo compounds to difluorocarbene followed by elimination of N-2. Compared to previously reported Cu-catalyzed gem-difluoroolefination of diazo compounds with TMSCF3, which possesses a narrow substrate scope due to a demanding requirement on the reactivity of diazo compounds and in-situ-generated CuCF3, this transition-metal-free protocol affords a general and efficient approach to various disubstituted 1,1-difluoroalkenes, including difluoroacrylates, diaryldifluoroolefins, as well as arylalkyldifluoroolefins. In view of the ready availability of diazo compounds and difluorocarbene reagents and versatile transformations of 1,1-difluoroalkenes, this new gem-difluoroolefination method is expected to find wide applications in organic synthesis. |
| 学科主题 | 氟化学 |
| 收录类别 | SCI |
| 原文出处 | http://dx.doi.org/10.1021/jacs.5b09888 |
| 语种 | 英语 |
| WOS记录号 | WOS:000365148500037 |
| 源URL | [http://ir.sioc.ac.cn/handle/331003/39764]  |
| 专题 | 上海有机化学研究所_中科院有机氟化学重点实验室 |
| 作者单位 | 1.中科院上海有机化学研究所, 有机氟化学重点实验室 2.Merck Research Laboratories |
| 推荐引用方式 GB/T 7714 | Hu MY,Ni CF,Li LC,et al. gem-Difluoroolefination of Diazo Compounds with TMSCF3 or TMSCF2Br: Transition-Metal-Free Cross-Coupling of Two Carbene Precursors[J]. J. Am. Chem. Soc.,2015,137(45):14496-14501. |
| APA | 胡明友,倪传法,李铃春,韩永新,&胡金波.(2015).gem-Difluoroolefination of Diazo Compounds with TMSCF3 or TMSCF2Br: Transition-Metal-Free Cross-Coupling of Two Carbene Precursors.J. Am. Chem. Soc.,137(45),14496-14501. |
| MLA | 胡明友,et al."gem-Difluoroolefination of Diazo Compounds with TMSCF3 or TMSCF2Br: Transition-Metal-Free Cross-Coupling of Two Carbene Precursors".J. Am. Chem. Soc. 137.45(2015):14496-14501. |
入库方式： OAI收割
来源：上海有机化学研究所
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