N-acylsulfonamide linker activation by Pd-catalyzed allylation.

Organic letters (2006-06-02)
Yi He, Jesse P Wilkins, Laura L Kiessling

N-Acylsulfonamide safety-catch linkers are versatile tools in solid-phase organic synthesis because of their stability. This stability necessitates linker activation prior to compound cleavage. Here, we demonstrate that the N-acylsulfonamide group can react with a pi-allyl palladium complex and that these mild and neutral conditions can be exploited for linker activation. The advantages of this process are illustrated by its use in the efficient synthesis of thioesters. We anticipate that this activation method will extend the utility of the N-acylsulfonamide group. [reaction: see text]

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HATU, 97%
HATU, ≥98.0% (CHN)