Palau’Chlor^®: Easily and Selectively Functionalize Lead Compounds

Introduction

Aryl chlorides are commonly used in cross-coupling reactions and can serve as key intermediates towards the synthesis of pharmaceutical drug candidates and natural products. Therefore, the addition of chlorine onto synthetic compounds can lead to the diversity of functionalized compounds. Current chlorination reagents include SO₂Cl₂ or Cl₂ which can pose safety hazards due their high reactivity. Alternatively, N-chlorosuccinimide is safer to handle but has a decreased reactivity profile. Palau’Chlor^® (792454) is a bench-stable chlorinating reagent offering adequate reactivity and high-selectivity.

Advantages

Previous chlorinating methods suffer from limited reactivity profiles or pose safety hazards. Palau’Chlor^® is a highly reactive chlorinating reagent that can be safely used on the bench-top using operationally simple reaction conditions. Furthermore, it is able to chlorinate molecules that are unreactive towards other chlorinating reagents. Palau’Chlor^® is compatible with many functional groups, thereby expanding the available heterocycles that can be functionalized. Although highly reactive, Palau’Chlor^® can selectively chlorinate heterocyclic lead compounds (in discrete and predictable locations) at any synthetic stage with minimal over-chlorination.

Representative Applications

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Reference

1. Rodriguez RA, Pan C, Yabe Y, Kawamata Y, Eastgate MD, Baran PS. 2014. Palau?chlor: A Practical and Reactive Chlorinating Reagent. J. Am. Chem. Soc.. 136(19):6908-6911. https://doi.org/10.1021/ja5031744