Insight into C4 Selectivity in the Light‐Driven C–H Fluoroalkylation of Pyridines and Quinolines

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(46)

Published: Aug. 9, 2024

Abstract Given the prevalence of pyridine motifs in FDA‐approved drugs, selective fluoroalkylation pyridines and quinolines is essential for preparing diverse bioisosteres. However, challenges are often faced with conventional Minisci reactions achieving precise regioselectivity owing to competing reaction sites limited availability fluoroalkyl radical sources. Herein, we present a light‐driven, C4‐selective azines utilizing N‐aminopyridinium salts readily available sulfinates. Our approach employs electron donor‐acceptor complexes, highly under mild conditions without an external photocatalyst. This practical method not only enables installation CF 2 H groups but also allows incorporation ‐alkyl functional entities, surpassing limitations previous methods. The versatility pathway further demonstrated through straightforward three‐component involving alkenes [1.1.1]propellane. Detailed experimental computational studies have elucidated origins regioselectivity, providing profound insights into mechanistic aspects.

Language: Английский

Selectfluor-triggered C–H halogenations of enaminones with copper(I) halide (CuX) for the synthesis of 3-halochromones

Zeitschrift für Naturforschung B, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 3, 2024

Abstract A practical and efficient synthetic route to construct a variety of 3-halochromones has been realized using Selectfluor reagent as fluorine source, or Selectfluor-copper(I) halide combination halogen source under mild conditions. This reaction proceeds via sequence electrophilic cation addition, cyclization leading broad range in good excellent yields short period time. Additionally, the utilization commercially available cost-effective copper(I) renders this system highly practical.

Language: Английский