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Kennedy, C. Rose; Lin, Song; Jacobsen, Eric N.
Angewandte Chemie, October 4, 2016, Volume: 55, Issue: 41Journal Article
Catalysis by small molecules (≤1000 Da, 10−9 m) that are capable of binding and activating substrates through attractive, noncovalent interactions has emerged as an important approach in organic and organometallic chemistry. While the canonical noncovalent interactions, including hydrogen bonding, ion pairing, and π stacking, have become mainstays of catalyst design, the cation–π interaction has been comparatively underutilized in this context since its discovery in the 1980s. However, like a hydrogen bond, the cation–π interaction exhibits a typical binding affinity of several kcal mol−1 with substantial directionality. These properties render it attractive as a design element for the development of small‐molecule catalysts, and in recent years, the catalysis community has begun to take advantage of these features, drawing inspiration from pioneering research in molecular recognition and structural biology. This Review surveys the burgeoning application of the cation–π interaction in catalysis. Positive effects: This Review discusses the burgeoning role of the cation–π interaction in the small‐molecule catalysis of organic and organometallic reactions. An extensive survey of the state‐of‐the‐art research emphasizes how unexpected discoveries and systematic mechanistic studies have begun to enable rational applications of the cation–π interaction in catalyst design.
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