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DOI | 10.1038/ncomms14145 |
Chiral acid-catalysed enantioselective C-H functionalization of toluene and its derivatives driven by visible light | |
Li, Fuyuan1; Tian, Dong1; Fan, Yifan1,2; Lee, Richmond3; Lu, Gang4; Yin, Yanli1; Qiao, Baokun1; Zhao, Xiaowei1; Xiao, Ziwei1; Jiang, Zhiyong1,2 | |
2019-04-16 | |
发表期刊 | NATURE COMMUNICATIONS
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ISSN | 2041-1723 |
出版年 | 2019 |
卷号 | 10 |
文章类型 | Article |
语种 | 英语 |
国家 | Peoples R China; Singapore |
英文摘要 | Toluene and its derivatives are petroleum-derived raw materials produced from gasoline by catalytic reformation. These abundant chemical feedstocks are commonly used as solvents in organic synthesis. The C(sp(3))-H functionalization of these unactivated substrates has been widely used to directly introduce benzylic motifs into diverse molecules to furnish important compounds. Despite these advances, progress in asymmetric catalysis remains underdeveloped. Here, we report photoinduced radical-based enantioselective C(sp(3))-C(sp(3)) coupling reactions of activated ketones with toluene and its derivatives by means of chiral acid catalysis. With a La(OTf)(3)/pybox complex catalyst, a variety of chiral 3-hydroxy-3-benzyl-substituted 2-oxindoles, including many conventionally difficult-to-access variants, are obtained directly from isatins in high yields with good to excellent enantioselectivities. Acenaphthoquinone is also compatible with the use of a chiral phosphoric acid (CPA) catalyst, leading to another series of important enantioenriched tertiary alcohols. |
领域 | 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000464654700013 |
WOS关键词 | PHOTOREDOX ; HYDROXYLATION ; C(SP(3))-H ; ALKYLATION ; OXINDOLES ; RADICALS ; PHOTOREACTIONS ; 1-ACETYLISATIN ; CONSTRUCTION ; FLUORINATION |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
URL | 查看原文 |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/203184 |
专题 | 资源环境科学 |
作者单位 | 1.Henan Univ, Key Lab Nat Med & Immunoengn Henan Prov, Kaifeng 475004, Henan, Peoples R China; 2.Henan Normal Univ, Sch Chem & Chem Engn, Key Lab Green Chem Media & React, Minist Educ, Xinxiang 453007, Henan, Peoples R China; 3.Singapore Univ Technol & Design, Singapore 487372, Singapore; 4.Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Shandong, Peoples R China |
推荐引用方式 GB/T 7714 | Li, Fuyuan,Tian, Dong,Fan, Yifan,et al. Chiral acid-catalysed enantioselective C-H functionalization of toluene and its derivatives driven by visible light[J]. NATURE COMMUNICATIONS,2019,10. |
APA | Li, Fuyuan.,Tian, Dong.,Fan, Yifan.,Lee, Richmond.,Lu, Gang.,...&Jiang, Zhiyong.(2019).Chiral acid-catalysed enantioselective C-H functionalization of toluene and its derivatives driven by visible light.NATURE COMMUNICATIONS,10. |
MLA | Li, Fuyuan,et al."Chiral acid-catalysed enantioselective C-H functionalization of toluene and its derivatives driven by visible light".NATURE COMMUNICATIONS 10(2019). |
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