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- W3048697903 abstract "We report reductive alkylation reactions of amines using carboxylic acids as nominal electrophiles. The two-step reaction exploits the dual reactivity of phenylsilane and involves a silane-mediated amidation followed by a Zn(OAc)2-catalyzed amide reduction. The reaction is applicable to a wide range of amines and carboxylic acids and has been demonstrated on a large scale (305 mmol of amine). The rate differential between the reduction of tertiary and secondary amide intermediates is exemplified in a convergent synthesis of the antiretroviral medicine maraviroc. Mechanistic studies demonstrate that a residual 0.5 equivalents of carboxylic acid from the amidation step is responsible for the generation of silane reductants with augmented reactivity, which allow secondary amides, previously unreactive in zinc/phenylsilane systems, to be reduced." @default.
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- W3048697903 date "2020-01-01" @default.
- W3048697903 modified "2023-10-15" @default.
- W3048697903 title "A practical catalytic reductive amination of carboxylic acids" @default.
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- W3048697903 doi "https://doi.org/10.1039/d0sc02271c" @default.
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