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

Leejae Kim,

Wooseok Lee, Sungwoo Hong

et al.

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

Copper-Catalyzed Diastereoselective Addition of a [1,1,1]Propellane Dimer to N-tert-Butanesulfinyl Aldimines DOI
Yihui Li,

Yuan Han,

Jia-Xuan Luo

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 21, 2025

[1,1,1]Propellane is typically used as a building block for the construction of bicyclo[1,1,1]pentanes and cyclobutanes. In this work, diverse chiral bi(methylenecyclobutylidene) complexes were synthesized by diastereoselective addition [1,1,1]propellane dimer to N-tert-butanesulfinyl aldimines in presence copper bipyridine. Density functional theory calculations revealed that both step regeneration catalyst contributed generation favored (Ss,S,S)-diastereomer.

Language: Английский

Citations

0
Photocatalytic Difunctionalization of [1.1.1]Propellane DOI Open Access
Tanmay Das, M. F. Mohär, Alakananda Hajra

et al.

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: March 27, 2025

The hunt for new molecular structures to improve the efficacy of biologically active molecules is at forefront pharmaceutical chemistry. So synthetic chemists have always been busy in last few decades synthesizing and testing frameworks which would work as more efficient bioisosteres present bioactive functional groups. In this area, bicyclo[1.1.1]pentane (BCP) framework has identified a promising candidate. It being utilized bioisostere aryl, tert-butyl, alkynes, etc. Now major precursor various BCP derivatives [1.1.1]propellane functionalization drawn widespread attention organic chemist community. Over past two decades, use visible light synthesis rapidly gained popularity, it represents one most approaches aligned with principles green sustainable chemistry, several interesting papers covering photocatalytic difunctionalization also published decade. This particular field really attracted That why we decided compile review article articles related under conditions. Here review, categorized discussed three categories, namely i) without using any catalyst, ii) organocatalysts, iii) metal catalysts deeper understanding key aspects these transformations.

Language: Английский

Citations

0
Insight into C4 Selectivity in the Light‐Driven C–H Fluoroalkylation of Pyridines and Quinolines DOI

Leejae Kim,

Wooseok Lee, Sungwoo Hong

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(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

Citations

2
Insight into C4 Selectivity in the Light‐Driven C–H Fluoroalkylation of Pyridines and Quinolines DOI

Leejae Kim,

Wooseok Lee, Sungwoo Hong

et al.

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

Citations

0