Electrophilic halogenation of arenes has been well studied. However, an efficient method that allows for the safe and convenient halogenation of deactivated arenes is still sought after. Using N-halosuccinimides (NXS) as halogenating agents in the presence of BF3 monohydrate as a strong acid catalyst, halogenation of many deactivated aromatics has been achieved earlier in our laboratory. But its general application is sometimes limited due to high vapor pressure, corrosive nature and greater difficulty in handling the acid catalyst. We have found that methanesulfonic acid (MsOH) is an excellent liquid Bronsted acid catalyst for the efficient halogenation of both activated and deactivated arenes. MsOH is much safer and easy to handle, commercially available, and more tolerant to various functional groups compared to other acid catalysts invoked for this transformation. The details of this study will be presented.

N-halosuccinimides-methanesulfonic acid: A safe, efficient and powerful electrophilic halogenation system for arenes

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