Superelectrophilic Reactions in Organic Synthesis
Summary
Superelectrophilic reactions harness highly charged intermediates—dications, trications or higher—to engage even the most inert nucleophiles under carefully controlled acidic conditions. By subjecting pro-electrophiles to superacidic media or dual Brønsted acid activation, researchers generate multicationic species whose enhanced electrophilicity enables transformations that would be unattainable with conventional monocationic reagents. This approach has been applied to aromatic acylations, amidations, hydroarylations and rearrangement processes, delivering new routes to complex natural products, pharmaceutically relevant scaffolds and functional materials. Key advances include the strategic use of weakly coordinating anions to stabilise reactive centres, the design of substrates bearing multiple ionisable groups for tandem cyclisations, and the development of milder acid systems that balance reactivity with operational safety. The global significance of superelectrophilic methods lies in their capacity to streamline synthetic sequences, reduce reliance on metal catalysts and unlock pathways to novel compound classes.
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Superelectrophilic Reactions in Organic Synthesis publication trend
The graph below shows the total number of articles in superelectrophilic reactions in organic synthesis across all publications each year (not limited to Nature Index journals).
Technical terms
Superelectrophile: A highly charged cationic species (dication or higher) with enhanced propensity to react with weak nucleophiles.
Superacid: An acid stronger than 100% sulfuric acid, capable of protonating very weak bases to form superelectrophilic intermediates.
Acylium cation: A positively charged species (R–C≡O⁺) generated by protonation or ionisation of carboxylic derivatives, central to superelectrophilic acylations.
Brønsted acid assisted Brønsted acid catalysis: A strategy using one acid to enhance the proton-donating ability of another, enabling formation of multiprotonated electrophiles.
References
- Superelectrophilic Activation of Phosphacoumarins towards Weak Nucleophiles via Brønsted Acid Assisted Brønsted Acid Catalysis. International Journal of Molecular Sciences (2024).
- Superelectrophiles: Recent Advances. Molecules (2020).
- Friedel-Crafts-Type Acylation and Amidation Reactions in Strong Brønsted Acid: Taming Superelectrophiles †. Molecules (2022).
- Superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups. Beilstein Journal of Organic Chemistry (2019).
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