Iodine(III)‐Based Halogen Bond Donors: Properties and Applications

• Published in: Chemical record Vol. 21; no. 8; pp. 1912 - 1927
• Main Authors: Robidas, Raphaël, Reinhard, Dominik L., Legault, Claude Y., Huber, Stefan M.
• Format: Journal Article
• Language: English
• Published: Hoboken Wiley Subscription Services, Inc 01.08.2021
• Subjects: Bonding strength; Catalysts; Diaryliodonium; Donors (electronic); Halogen bonding; Hypervalent iodine; Iodine; Iodolium; Lewis acidity
• ISSN: 1527-8999; 1528-0691; 1528-0691
• DOI: 10.1002/tcr.202100119

Halogen bonding, the non‐covalent interaction of Lewis bases with an electron‐deficient region of halogen substituents, received increased attention recently. Consequently, the design and evaluation of numerous halogen‐containing species as halogen bond donors have been subject to intense research. More recently, organoiodine compounds at the iodine(III) state have been receiving growing attention in the field. Due to their electronic and structural properties, they provide access to unique binding modes. For this reason, our groups have been involved in the development of such compounds, in the quantification of their halogen bonding strength (through the evaluation of their Lewis acidities), as well as in the evaluation of their activities as catalysts in several model reactions. This account will describe these contributions. Iodine(III)‐based halogen bond donors (halogen‐based Lewis acids) have received increasing attention lately. This account provides an overview of the topic and summarizes our studies on Lewis acidity measurements and applications in catalysis.