Abstract
Halogen bonding has received a significant increase in attention in the past 20 years. An important part of this interest has centered on catalytic applications of halogen bonding. Halogen bond (XB) catalysis is still a developing field in organocatalysis, although XB catalysis has outgrown its proof of concept phase. The start of this year witnessed the publication of the first example of a purely XB-based enantioselective catalytic reaction. While the selectivity can be improved upon, there are already plenty of examples in which halogen bonds, among other interactions, play a crucial role in the outcome of highly enantioselective reactions. This paper will give an overview of the current state of the use of XBs in catalytic stereoselective processes.
Highlights
Halogen bonding is an attractive interaction between an electrophilic region associated with a halogen atom and a nucleophilic region (Desiraju et al, 2013)
As the coordination patterns in hypervalent iodine species can be viewed as special cases of halogen bonding (Heinen et al, 2020; Turunen and Erdélyi, 2020) and as XBs can contribute to halogen insertions, it is pertinent to mention this type of catalysis in the review
It should be noted that several chiral XB donors have been featured in publications on XB catalysis (Kniep et al, 2012; FIGURE 8 | (A) Enantioselective Mannich reaction; (B) catalysts probed to determine the influence of the halogen atom on the reaction; (C) proposed catalytic cycle
Summary
Halogen bonding has received a significant increase in attention in the past 20 years. An important part of this interest has centered on catalytic applications of halogen bonding. Halogen bond (XB) catalysis is still a developing field in organocatalysis, XB catalysis has outgrown its proof of concept phase. The start of this year witnessed the publication of the first example of a purely XB-based enantioselective catalytic reaction. While the selectivity can be improved upon, there are already plenty of examples in which halogen bonds, among other interactions, play a crucial role in the outcome of highly enantioselective reactions. This paper will give an overview of the current state of the use of XBs in catalytic stereoselective processes.
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