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Synthesis
DOI: 10.1055/a-2681-5829
DOI: 10.1055/a-2681-5829
Short Review
Charge-Enhanced Hydrogen Bond and Brønsted Acid Catalysis: An Evolving Frontier
Supported by: NSERC RGPIN2025-04511
Funding Information The authors are grateful to the Natural Sciences and Engineering Research Council (NSERC) for financial support. T.D. thanks the NSERC for Discovery Grant (RGPIN2025-04511). S.V. thanks the NSERC for PGS-D funding. N. K. thanks OGS for funding.
Abstract
In catalysis, both rate acceleration and selectivity are of central importance, and strategies to achieve these outcomes remain fundamental to advancing synthetic methodology. Over the past two decades, the merger of traditional catalytic paradigms with charge-enhancing elements has led to unprecedented reactivity in bond-forming processes with broad synthetic utility. These systems augmented by charge are increasingly attracting attention for their unique modes of activation. In particular, this review highlights and contextualizes recent advancements in charge-enhanced hydrogen bond and Brønsted acid catalysis that enable novel activation modes complementary to traditional catalytic platforms. Special emphasis is placed on catalysts such as amidinium, cyclopropenium, and azolium ions as well as cationic thiourea and phosphoric acids, whose charge-enhanced features have enabled transformative improvements in reactivity, rate acceleration, and selectivity.
Keywords
Hydrogen-bonding - Brønsted acidity - Stereoselectivity - Rate-enhancement - Cyclopropenium - Phosphoric acid - Thiourea - AmidiniumPublication History
Received: 05 June 2025
Accepted after revision: 11 August 2025
Article published online:
27 August 2025
© 2025. Thieme. All rights reserved.
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