B(MIDA)-directed site-selective intermolecular halofluoroalkylation of alkenes: synthesis of diversely functionalized building blocks
文献类型：期刊论文
| 作者 | Wu, Hengbo2,3; Luo, Ruitong2,3; Peng, Jingjing2,3; Han, Zijian2,3; Zhang, Renjie1,2; Xu, Zhijian2,3 ; Zhu, Weiliang2,3; Liu, Hong1,2,3; Li, Chunpu1,2,3
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| 刊名 | CHEMICAL SCIENCE
 |
| 出版日期 | 2025-01-10 |
| 页码 | 8 |
| ISSN号 | 2041-6520 |
| DOI | 10.1039/d4sc07900k |
| 英文摘要 | alpha-Halo borides are generally constructed via Matteson homologation, and the synthesis of both fluorinated and functionalized ambiphilic boronates is challenging and has received inadequate attention. Herein, we describe the N-methyliminodiacetyl boronate [B(MIDA)]-directed halogenation of alkenes via a complementary sequence involving fluoroalkyl radical addition followed by guided radical-to-metal oxidative addition and C-X reductive elimination. The alkali cation and functional groups in B(MIDA) enable coulombic interaction and weak attraction with halogens, which could weaken the Pd-X bond and assist in C-X bond formation and is verified by DFT calculations. As a result, a wide variety of highly functionalized fluorinated alpha-halo boronates, including drugs and natural products, are obtained in good or moderate yields through the unique catalytic manifold. Notably, the trifunctionalized (F, X, B) building block could be transformed into diverse modified fluorinated products. |
| WOS关键词 | HECK-TYPE REACTION ; BORONIC ESTERS ; ASYMMETRIC-SYNTHESIS ; GENERAL-SOLUTION ; ACCESS ; ACIDS ; HOMOLOGATION ; COMPLEXES ; PALLADIUM |
| 资助项目 | National Key Research and Development Program of China[2023YFF1205104] ; National Key Research and Development Program of China[2022YFA1302900] ; National Key R&D Program of China[82273766] ; National Key R&D Program of China[82130105] ; National Natural Science Foundation of China[2020282] ; Youth Innovation Promotion Association CAS |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:001393039200001 |
| 出版者 | ROYAL SOC CHEMISTRY |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/315627]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | Zhu, Weiliang; Liu, Hong; Li, Chunpu |
| 作者单位 | 1.Univ Chinese Acad Sci, Hangzhou Inst Adv Study, Sch Pharmaceut Sci & Technol, Hangzhou 310024, Peoples R China 2.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Wu, Hengbo,Luo, Ruitong,Peng, Jingjing,et al. B(MIDA)-directed site-selective intermolecular halofluoroalkylation of alkenes: synthesis of diversely functionalized building blocks[J]. CHEMICAL SCIENCE,2025:8. |
| APA | Wu, Hengbo.,Luo, Ruitong.,Peng, Jingjing.,Han, Zijian.,Zhang, Renjie.,...&Li, Chunpu.(2025).B(MIDA)-directed site-selective intermolecular halofluoroalkylation of alkenes: synthesis of diversely functionalized building blocks.CHEMICAL SCIENCE,8. |
| MLA | Wu, Hengbo,et al."B(MIDA)-directed site-selective intermolecular halofluoroalkylation of alkenes: synthesis of diversely functionalized building blocks".CHEMICAL SCIENCE (2025):8. |
入库方式： OAI收割
来源：上海药物研究所
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