C−H Borylation Techniques in Organic Synthesis

Carbon–hydrogen borylation has emerged as a transformative strategy in organic synthesis, enabling the direct conversion of unactivated C–H bonds into versatile carbon–boron bonds. This approach circumvents the need for prefunctionalised substrates, offering enhanced atom economy and step efficiency. A broad spectrum of catalysts—most notably iridium, cobalt and main-group species—has been developed, each exploiting distinct mechanistic pathways including oxidative addition, σ-bond metathesis and electrophilic C–H activation. Advances in ligand design, particularly through the incorporation of directing groups and noncovalent interactions, have refined site selectivity, allowing ortho, meta and para functionalisation of (hetero)arenes under mild conditions. The field now extends beyond precious-metal platforms, with sustainable alternatives and metal-free protocols yielding high turnover numbers and broad substrate scope. These techniques underpin the rapid assembly of complex molecular frameworks, with applications in pharmaceuticals, agrochemicals and materials science. Ongoing efforts focus on enhancing regio- and chemoselectivity, expanding substrate diversity and integrating C–H borylation into cascade sequences for streamlined synthesis.

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C−H Borylation Techniques in Organic Synthesis publication trend

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Technical terms

C–H borylation: Direct conversion of a carbon–hydrogen bond into a carbon–boron bond.

Directing group: A functional moiety that coordinates to a catalyst to control regioselectivity.

Oxidative addition: A step in which a metal inserts into a covalent bond, increasing its oxidation state.

Reductive elimination: A process where two ligands on a metal centre combine and depart, reducing the metal’s oxidation state.

Regioselectivity: Preference for reaction at one position over others in a molecule.

References

1. Main Group Catalyzed Arene Borylation: Challenges and Opportunities. ACS Catalysis (2023).
2. C–H Activation: Toward Sustainability and Applications. ACS Central Science (2021).
3. Cobalt-Catalyzed C–H Borylation. Journal of the American Chemical Society (2014).
4. Harnessing non-covalent interactions to exert control over regioselectivity and site-selectivity in catalytic reactions. Chemical Science (2017).