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DOI | 10.1126/science.aar7335 |
Modular radical cross-coupling with sulfones enables access to sp(3)-rich (fluoro)alkylated scaffolds | |
Merchant, Rohan R.1; Edwards, Jacob T.1; Qin, Tian1; Kruszyk, Monika M.1; Bi, Cheng1; Che, Guanda2; Bao, Deng-Hui2; Qiao, Wenhua2; Sun, Lijie2; Collins, Michael R.3; Fadeyi, Olugbeminiyi O.4; Gallego, Gary M.3; Mousseau, James J.4; Nuhant, Philippe4; Baran, Phil S.1 | |
2018-04-06 | |
发表期刊 | SCIENCE
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ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2018 |
卷号 | 360期号:6384页码:75-80 |
文章类型 | Article |
语种 | 英语 |
国家 | USA; Peoples R China |
英文摘要 | Cross-coupling chemistry is widely applied to carbon-carbon bond formation in the synthesis of medicines, agrochemicals, and other functional materials. Recently, single-electron-induced variants of this reaction class have proven particularly useful in the formation of C(sp(2))-C(sp(3)) linkages, although certain compound classes have remained a challenge. Here, we report the use of sulfones to activate the alkyl coupling partner in nickel-catalyzed radical cross-coupling with aryl zinc reagents. This method's tolerance of fluoroalkyl substituents proved particularly advantageous for the streamlined preparation of pharmaceutically oriented fluorinated scaffolds that previously required multiple steps, toxic reagents, and nonmodular retrosynthetic blueprints. Five specific sulfone reagents facilitate the rapid assembly of a vast set of compounds, many of which contain challenging fluorination patterns. |
领域 | 地球科学 ; 气候变化 ; 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000429263100049 |
WOS关键词 | REDOX-ACTIVE ESTERS ; FLUORINATED SULFONES ; GRIGNARD-REAGENTS ; NICKEL CATALYSIS ; BORONIC ACIDS ; ARYL HALIDES ; PHOTOREDOX ; CONSTRUCTION ; ALKYLATION ; IODIDES |
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/198337 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Scripps Res Inst TSRI, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA; 2.Asymchem Life Sci Tianjin, Tianjin Econ Technol Dev Zone, Tianjin 300457, Peoples R China; 3.La Jolla Labs, Dept Chem, 10770 Sci Ctr Dr, San Diego, CA 92121 USA; 4.Pfizer Med Sci, Eastern Point Rd, Groton, CT 06340 USA |
推荐引用方式 GB/T 7714 | Merchant, Rohan R.,Edwards, Jacob T.,Qin, Tian,et al. Modular radical cross-coupling with sulfones enables access to sp(3)-rich (fluoro)alkylated scaffolds[J]. SCIENCE,2018,360(6384):75-80. |
APA | Merchant, Rohan R..,Edwards, Jacob T..,Qin, Tian.,Kruszyk, Monika M..,Bi, Cheng.,...&Baran, Phil S..(2018).Modular radical cross-coupling with sulfones enables access to sp(3)-rich (fluoro)alkylated scaffolds.SCIENCE,360(6384),75-80. |
MLA | Merchant, Rohan R.,et al."Modular radical cross-coupling with sulfones enables access to sp(3)-rich (fluoro)alkylated scaffolds".SCIENCE 360.6384(2018):75-80. |
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