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- Title
Reactivity Umpolung of Tertiary Amide Enabled by Catalytic Reductive Stannylation.
- Authors
Shi, Qiu; Liu, Wenbo H.
- Abstract
Reactivity umpolung is an important concept in organic chemistry. Established reactivity umpolung mainly focuses on the aldehyde and umpolung of amide carbonyl group is not known. In this report, we describe a process to obtain the umpolung reactivity of tertiary amide. This process hinges on the efficient reductive stannylation catalyzed by Ir/silane and facile Sn−Li exchange. By leveraging this umpolung reactivity, drug Fluoxetine was derivatized to 12 different analogues via reacting with various electrophiles and four biologically active molecules were prepared concisely. This unlocked umpolung reactivity of tertiary amide is expected to find applications to synthesize complex amines from amides.
- Subjects
UMPOLUNG; AMINATION; AMIDES; ORGANIC chemistry; CARBONYL group; ELECTROPHILES; FLUOXETINE
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 37, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202309567