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<p>Alkane C(sp<sup>3</sup>)–H borylation has emerged as a transformative strategy for converting inert hydrocarbons into versatile synthetic intermediates. This review comprehensively examines the evolution from stoichiometric reactions to sophisticated catalytic systems, emphasizing the central challenge of achieving precise selectivity control. We systematically analyze diverse methodologies, including transition metal-catalyzed approaches (Ir, Rh, Ru), and crucially, the rapidly evolving field of earth-abundant metal catalysis (Fe, Cu) and photoelectrochemical strategies. We detail radical-mediated strategies employing hydrogen atom transfer (HAT) through various activation modes, substrate-controlled site-selective functionalization, and asymmetric methods for enantioselective C–B bond formation. Beyond a general overview, we critically analyze underlying mechanisms, highlighting the complex interplay between steric and electronic factors in determining unconventional site-selectivity in radical pathways. Recent advances in ligand design, catalyst architecture, and innovative activation strategies have significantly expanded the scope of this methodology, enabling breakthroughs in challenging transformations, including selective methane functionalization and complex molecule editing.</p>

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Alkane C(sp3)–H borylation: concepts, classifications, mechanisms, and applications

  • 期刊论文

  • 发表日期：

    2026年5月26日

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  • Jia-Lin Tu,
  • Yiwen Xia,
  • Lin Guo,
  • Wujiong Xia

摘要

Alkane C(sp3)–H borylation has emerged as a transformative strategy for converting inert hydrocarbons into versatile synthetic intermediates. This review comprehensively examines the evolution from stoichiometric reactions to sophisticated catalytic systems, emphasizing the central challenge of achieving precise selectivity control. We systematically analyze diverse methodologies, including transition metal-catalyzed approaches (Ir, Rh, Ru), and crucially, the rapidly evolving field of earth-abundant metal catalysis (Fe, Cu) and photoelectrochemical strategies. We detail radical-mediated strategies employing hydrogen atom transfer (HAT) through various activation modes, substrate-controlled site-selective functionalization, and asymmetric methods for enantioselective C–B bond formation. Beyond a general overview, we critically analyze underlying mechanisms, highlighting the complex interplay between steric and electronic factors in determining unconventional site-selectivity in radical pathways. Recent advances in ligand design, catalyst architecture, and innovative activation strategies have significantly expanded the scope of this methodology, enabling breakthroughs in challenging transformations, including selective methane functionalization and complex molecule editing.