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20.4.1.1.7 Method 7: Activation of Acid Chlorides Using Pyridine-2-thiones

DOI: 10.1055/sos-SD-020-00605

Keller, P. A.Science of Synthesis, (200720631.

The reaction of acid chlorides, e.g. 47, with pyridine-2-thiones gives water-soluble 2-(benzoylsulfanyl)-1-methylpyridinium salts which can react with carboxylate anions 48 to yield mixed or symmetrical (for R1=Ph) anhydrides 49 (Scheme 20).[‌64‌] Thus far, the pyridinium salt used has been based on benzoyl chloride; however, this could easily be extended further.

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