Copper-catalyzed radical c-c bond cleavage and [4+1] annulation cascade of cycloketone oxime esters with enaminothiones
文献类型：期刊论文
| 作者 | He, Yuan1,2; Lou, Jiang1,2; Wu, Kaikai1; Wang, Hongmei3; Yu, Zhengkun1,4 |
| 刊名 | Journal of organic chemistry
 |
| 出版日期 | 2019-02-15 |
| 卷号 | 84期号:4页码:2178-2190 |
| ISSN号 | 0022-3263 |
| DOI | 10.1021/acs.joc.8b03175 |
| 通讯作者 | Wang, hongmei(wanghongmei@dicp.ac.cn) ; Yu, zhengkun(zkyu@dicp.ac.cn) |
| 英文摘要 | Carbon-carbon bond formation is among the most important reactions in organic synthesis. reconstruction of a carbon-carbon bond through ring-opening c-c bond cleavage of a strained carbocycle usually occurs via a thermodynamically preferable pathway. however, carbon-carbon bond formation through thermodynamically less favorable c-c bond cleavage has seldom been documented. herein, we disclose an unusual c-c bond cleavage of cycloketone oxime esters for [4+1] annulation. under anaerobic copper(i) catalysis, cycloketone oxime esters underwent regioselective, thermodynamically less favorable radical c-c bond cleavage followed by annulation with enaminothiones; that is, alpha-thioxo ketene n,s-acetals efficiently affording 2-cyanoalkylaminothiophene derivatives. cyclobutanone, -pentanone, -hexanone, and -heptanone oxime esters could act as the effective cl building blocks in the annulation reaction. an iminyl radical mechanism is proposed for the rare c-c bond cleavage/[4+1] annulation cascade. |
| WOS关键词 | CYCLOBUTANONE O-BENZOYLOXIMES ; KETENE N,S-ACETALS ; IMINYL RADICALS ; THIOBENZOYLKETENE S,N-ACETALS ; THIOAROYLKETENE S,N-ACETALS ; H CYANOALKYLATION ; N-TOSYLHYDRAZONES ; RING-CLEAVAGE ; REAGENTS ; ACCESS |
| WOS研究方向 | Chemistry |
| WOS类目 | Chemistry, Organic |
| 语种 | 英语 |
| WOS记录号 | WOS:000459367100050 |
| 出版者 | AMER CHEMICAL SOC |
| URI标识 | http://www.irgrid.ac.cn/handle/1471x/2372675 |
| 专题 | 大连化学物理研究所 |
| 通讯作者 | Wang, Hongmei; Yu, Zhengkun |
| 作者单位 | 1.Chinese Acad Sci, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 3.State Key Lab NBC Protect Civilian, Beijing 102205, Peoples R China 4.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R China |
| 推荐引用方式 GB/T 7714 | He, Yuan,Lou, Jiang,Wu, Kaikai,et al. Copper-catalyzed radical c-c bond cleavage and [4+1] annulation cascade of cycloketone oxime esters with enaminothiones[J]. Journal of organic chemistry,2019,84(4):2178-2190. |
| APA | He, Yuan,Lou, Jiang,Wu, Kaikai,Wang, Hongmei,&Yu, Zhengkun.(2019).Copper-catalyzed radical c-c bond cleavage and [4+1] annulation cascade of cycloketone oxime esters with enaminothiones.Journal of organic chemistry,84(4),2178-2190. |
| MLA | He, Yuan,et al."Copper-catalyzed radical c-c bond cleavage and [4+1] annulation cascade of cycloketone oxime esters with enaminothiones".Journal of organic chemistry 84.4(2019):2178-2190. |
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