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Metal-free directed sp2-C-H borylation.
Lv, Jiahang; Chen, Xiangyang; Xue, Xiao-Song; Zhao, Binlin; Liang, Yong; Wang, Minyan; Jin, Liqun; Yuan, Yu; Han, Ying; Zhao, Yue; Lu, Yi; Zhao, Jing; Sun, Wei-Yin; Houk, Kendall N; Shi, Zhuangzhi.
Afiliação
  • Lv J; State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.
  • Chen X; College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, China.
  • Xue XS; Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, USA.
  • Zhao B; Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, USA.
  • Liang Y; State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin, China.
  • Wang M; State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.
  • Jin L; State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.
  • Yuan Y; State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.
  • Han Y; College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, China.
  • Zhao Y; College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, China.
  • Lu Y; College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, China.
  • Zhao J; State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.
  • Sun WY; State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.
  • Houk KN; State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.
  • Shi Z; State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.
Nature ; 575(7782): 336-340, 2019 11.
Article em En | MEDLINE | ID: mdl-31723273
ABSTRACT
Organoboron reagents are important synthetic intermediates that have a key role in the construction of natural products, pharmaceuticals and organic materials1. The discovery of simpler, milder and more efficient approaches to organoborons can open additional routes to diverse substances2-5. Here we show a general method for the directed C-H borylation of arenes and heteroarenes without the use of metal catalysts. C7- and C4-borylated indoles are produced by a mild approach that is compatible with a broad range of functional groups. The mechanism, which is established by density functional theory calculations, involves BBr3 acting as both a reagent and a catalyst. The potential utility of this strategy is highlighted by the downstream transformation of the formed boron species into natural products and drug scaffolds.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Boro / Compostos de Boro Idioma: En Ano de publicação: 2019 Tipo de documento: Article
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Boro / Compostos de Boro Idioma: En Ano de publicação: 2019 Tipo de documento: Article