Unraveling C4 selectivity in the light-driven C–H fluoroalkylation of pyridines and quinolines DOI Creative Commons
Sungwoo Hong,

Leejae Kim,

Wooseok Lee

и другие.

Опубликована: Май 28, 2024

Given the prevalence of pyridine motifs in FDA-approved drugs, selective fluoroalkylation pyridines and quinolines is essential for preparing diverse bioisosteres. However, conventional Minisci reactions often face challenges achieving precise regioselectivity due 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 CF2H groups but also allows incorporation CF2-alkyl with 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.

Язык: Английский

Unraveling C4 selectivity in the light-driven C–H fluoroalkylation of pyridines and quinolines DOI Creative Commons
Sungwoo Hong,

Leejae Kim,

Wooseok Lee

и другие.

Опубликована: Май 28, 2024

Given the prevalence of pyridine motifs in FDA-approved drugs, selective fluoroalkylation pyridines and quinolines is essential for preparing diverse bioisosteres. However, conventional Minisci reactions often face challenges achieving precise regioselectivity due 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 CF2H groups but also allows incorporation CF2-alkyl with 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.

Язык: Английский

Процитировано

1