Deoxygenative radical cross-coupling of C(sp3)-O/C(sp3)-H bonds promoted by hydrogen-bond interaction
文献类型：期刊论文
| 作者 | Wang, Yue2,3; Zhang, Suping1,2; Zeng, Ke2; Zhang, Pengli2; Song, Xiaorong2; Chen, Tie-Gen2,3; Xia, Guoqin2,3 |
| 刊名 | NATURE COMMUNICATIONS
 |
| 出版日期 | 2024-08-08 |
| 卷号 | 15期号:1页码:8 |
| DOI | 10.1038/s41467-024-50897-7 |
| 通讯作者 | Chen, Tie-Gen(chentiegen@simm.ac.cn) ; Xia, Guoqin(xiaguoqin@simm.ac.cn) |
| 英文摘要 | Building C(sp(3))-rich architectures using simple and readily available starting materials will greatly advance modern drug discovery. C(sp(3))-H and C(sp(3))-O bonds are commonly used to strategically disassemble and construct bioactive compounds, respectively. However, the direct cross coupling of these two chemical bonds to form C(sp(3))-C(sp(3)) bonds is rarely explored in existing literature. Conventional methods for forming C(sp(3))-C(sp(3)) bonds via radical-radical coupling pathways often suffer from poor selectivity, severely limiting their practicality in synthetic applications. In this study, we present a single electron transfer (SET) strategy that enables the cleavage of amine alpha-C - H bonds and heterobenzylic C - O bonds to form C(sp(3))-C(sp(3)) bonds. Preliminary mechanistic studies reveal a hydrogen bond interaction between substrates and phosphoric acid facilitates the cross-coupling of two radicals with high chemoselectivity. This methodology provides an effective approach to a variety of aza-heterocyclic unnatural amino acids and bioactive molecules. |
| WOS关键词 | C-H ACTIVATION ; ALKYL-HALIDES ; ACIDS ; DERIVATIVES ; ARYLATION ; ESTERS |
| 资助项目 | The 100 Talents Program of the Chinese Academy of Sciences ; National Natural Science Foundation of China[22271297] ; Program for Young Talented Investigators of Guangdong Province[2021QN020533] |
| WOS研究方向 | Science & Technology - Other Topics |
| 语种 | 英语 |
| WOS记录号 | WOS:001287600900010 |
| 出版者 | NATURE PORTFOLIO |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/312899]  |
| 专题 | 中国科学院上海药物研究所 |
| 通讯作者 | Chen, Tie-Gen; Xia, Guoqin |
| 作者单位 | 1.Guangzhou Univ Chinese Med, Guangzhou 510006, Peoples R China 2.Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Zhongshan, Peoples R China 3.Southern Med Univ, Sch Pharmaceut Sci, Guangzhou 510515, Peoples R China |
| 推荐引用方式 GB/T 7714 | Wang, Yue,Zhang, Suping,Zeng, Ke,et al. Deoxygenative radical cross-coupling of C(sp3)-O/C(sp3)-H bonds promoted by hydrogen-bond interaction[J]. NATURE COMMUNICATIONS,2024,15(1):8. |
| APA | Wang, Yue.,Zhang, Suping.,Zeng, Ke.,Zhang, Pengli.,Song, Xiaorong.,...&Xia, Guoqin.(2024).Deoxygenative radical cross-coupling of C(sp3)-O/C(sp3)-H bonds promoted by hydrogen-bond interaction.NATURE COMMUNICATIONS,15(1),8. |
| MLA | Wang, Yue,et al."Deoxygenative radical cross-coupling of C(sp3)-O/C(sp3)-H bonds promoted by hydrogen-bond interaction".NATURE COMMUNICATIONS 15.1(2024):8. |
入库方式： OAI收割
来源：上海药物研究所
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