Photoredox-mediated Minisci C–H alkylation of N-heteroarenes using boronic acids and hypervalent iodine† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc02653b Click here for additional data file.

نویسندگان

  • Guo-Xing Li
  • Christian A. Morales-Rivera
  • Yaxin Wang
  • Fang Gao
  • Gang He
  • Peng Liu
  • Gong Chen
چکیده

A photoredox-mediated Minisci C–H alkylation reaction of N-heteroarenes with alkyl boronic acids is reported. A broad range of primary and secondary alkyl groups can be efficiently incorporated into various N-heteroarenes using [Ru(bpy)3]Cl2 as photocatalyst and acetoxybenziodoxole as oxidant under mild conditions. The reaction exhibits excellent substrate scope and functional group tolerance, and offers a broadly applicable method for late-stage functionalization of complex substrates. Mechanistic experiments and computational studies suggest that an intramolecularly stabilized ortho-iodobenzoyloxy radical intermediate might play a key role in this reaction system.

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منابع مشابه

Correction: Photoredox-mediated Minisci C–H alkylation of N-heteroarenes using boronic acids and hypervalent iodine

Correction for 'Photoredox-mediated Minisci C-H alkylation of N-heteroarenes using boronic acids and hypervalent iodine' by Guo-Xing Li et al., Chem. Sci., 2016, DOI: ; 10.1039/c6sc02653b.

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Metal-free C–H alkylation of heteroarenes with alkyltrifluoroborates: a general protocol for 1°, 2° and 3° alkylation† †Electronic supplementary information (ESI) available: Experimental details and spectral data. See DOI: 10.1039/c7sc00283a Click here for additional data file.

A photoredox-catalyzed C–H functionalization of heteroarenes using a variety of primary, secondary, and tertiary alkyltrifluoroborates is reported. Using Fukuzumi's organophotocatalyst and a mild oxidant, conditions amenable for functionalizing complex heteroaromatics are described, providing a valuable tool for late-stage derivatization. The reported method addresses the three major limitation...

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A unified photoredox-catalysis strategy for C(sp3)–H hydroxylation and amidation using hypervalent iodine† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc02773g Click here for additional data file.

We report a unified photoredox-catalysis strategy for both hydroxylation and amidation of tertiary and benzylic C–H bonds. Use of hydroxyl perfluorobenziodoxole (PFBl–OH) oxidant is critical for efficient tertiary C–H functionalization, likely due to the enhanced electrophilicity of the benziodoxole radical. Benzylic methylene C–H bonds can be hydroxylated or amidated using unmodified hydroxyl ...

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عنوان ژورنال:

دوره 7  شماره 

صفحات  -

تاریخ انتشار 2016