Bibliographic Details
| Title: |
Selective Reductions of Complex Pyridines via NTf-Pyridinium Salts. |
| Authors: |
Josephitis, Celena1 (AUTHOR), McNally, Andrew1 (AUTHOR) Andy.McNally@colostate.edu |
| Source: |
Synthesis. Jun2026, Vol. 58 Issue 11, p1259-1264. 6p. |
| Subjects: |
Piperidine, Pyridinium compounds, Heterocyclic compounds, Hydrides, Catalysis, Chemical reduction, Pharmaceutical chemistry, Pyridine |
| Abstract: |
Piperidines are widely found in biologically active compounds, and accessing these N-heterocycles from pyridines is a commonly used strategy. However, this approach is challenging when pyridines are embedded in complex structures, such as those found in pharmaceutical compounds. Here, we present a sequential approach to piperidines that commences with a hydride addition to NTf-activated pyridinium salts. In this method, we combined tris(pentafluorophenyl)borane as a catalyst with a silane reducing agent to achieve 4-selective mono-reduction, and then combined it with metal-catalyzed reductions to obtain tetrahydropiperidine and piperidine derivatives. The process operates on a broad range of pyridines with various functional groups and substitution patterns, as well as on pyridine-containing drugs. [ABSTRACT FROM AUTHOR] |
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| Database: |
Engineering Source |
