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On-DNA Palladium-Catalyzed Hydrogenation-like Reaction Suitable for DNA-Encoded Library Synthesis. 2021
Julián Priego, and
Eduardo de Pedro Beato, and
Jesús Benavides, and
Adrián Gironda-Martínez, and
Fernando González, and
Jesús Blas, and
María Dolores Martín-Ortega, and
Ramón Rama-Garda, and
Jesús Ezquerra, and
Miguel A Toledo, and
Alicia Torrado
Centro de Investigación Lilly, S. A., 28108 Alcobendas, Madrid, Spain.
Herein we describe a method to orthogonally remove on-DNA N-Cbz, N-Alloc, N-Allyl, O-Bn, and O-Allyl protecting groups in the presence of other common protecting groups to afford free amines and carboxylic acids, respectively. The developed method uses NaBH4 as the source of hydrogen in the presence of Pd(OAc)2 under DNA aqueous conditions. In addition, under the developed conditions we were able to successfully hydrogenate triple and double bonds to totally saturated compounds. Furthermore, we introduce a new alternative procedure to reduce azides and aromatic nitro compounds to primary amines.
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