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Published on: February 20, 2020
Design Principles to Promote Acid-Base Interactions with a Weak Second-Sphere Lewis Acid
Alice L Atkins1, Matthias Zeller2, Nathaniel K Szymczak1
1Department of Chemistry, University of Michigan, Ann Arbor, Michigan48109, United States.
Abstract:
Boronic esters such as BPin are underutilized in secondary-sphere chemistry due to their weak acidity. We report a design strategy to enable cooperative binding with a BPin-appended NHC scaffold. Employing a shortened tether enhances preorganization and facilitates substrate binding in tandem with the metal center. Experimental and computational analyses clarify principles of the design that enable cooperativity.
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