Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers
Scherbinina S. I., Fedorov O. V., Levin V. V., Kokorekin V. A., Struchkova M. I., Dilman A. D.
Journal of Organic Chemistry
Vol.82, Issue24, P. 12967-12974
Опубликовано: 2017
Тип ресурса: Статья
DOI:10.1021/acs.joc.7b02467
Аннотация:
A method for the synthesis of diversely substituted 3-fluoropyridines from two ketone components is described. The reaction involves photoredox coupling of α,α-difluoro-β-iodoketones with silyl enol ethers catalyzed by fac-Ir(ppy)3 under blue LED irradiation with subsequent one-pot condensation with ammonium acetate. Based on cyclic voltammetry studies, it was determined that α,α-difluoro-β-iodoketones are reduced notably easier compared to 2,2,2-trifluoro-1-iodoethane, which may be ascribed to the influence of the carbonyl group. © 2017 American Chemical Society.
Ключевые слова:
Ethers; Iridium; Ketones; Ammonium acetate; Blue LEDs; Carbonyl groups; Ir(ppy)3; One pot condensation; Silyl enol ethers; Cyclic voltammetry; ammonia; ammonium acetate; ether derivative; hydrogen; iodide; iridium complex; ketone derivative; pyridine derivative; Article; catalysis; complex formation; controlled study; cyclic potentiometry; electron transport; fluorine nuclear magnetic resonance; high performance liquid chromatography; irradiation; phosphorus nuclear magnetic resonance; polymerization; reaction analysis; reduction (chemistry); silylation; synthesis; temperature sensitivity; ultraviolet spectroscopy
Язык текста: Английский
ISSN: 1520-6904
Scherbinina S. I.
Fedorov O. V.
Levin V. V.
Kokorekin V. A. Vladimir Alekseevich 1987-
Struchkova M. I.
Dilman A. D.
Счербинина С. И.
Федоров О. В.
Левин В. В.
Кокорекин В. А. Владимир Алексеевич 1987-
Стручкова М. И.
Дилман А. Д.
Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers
Текст визуальный непосредственный
Journal of Organic Chemistry
American Chemical Society
Vol.82, Issue24 P. 12967-12974
2017
Статья
Ethers Iridium Ketones Ammonium acetate Blue LEDs Carbonyl groups Ir(ppy)3 One pot condensation Silyl enol ethers Cyclic voltammetry ammonia ammonium acetate ether derivative hydrogen iodide iridium complex ketone derivative pyridine derivative Article catalysis complex formation controlled study cyclic potentiometry electron transport fluorine nuclear magnetic resonance high performance liquid chromatography irradiation phosphorus nuclear magnetic resonance polymerization reaction analysis reduction (chemistry) silylation synthesis temperature sensitivity ultraviolet spectroscopy
A method for the synthesis of diversely substituted 3-fluoropyridines from two ketone components is described. The reaction involves photoredox coupling of α,α-difluoro-β-iodoketones with silyl enol ethers catalyzed by fac-Ir(ppy)3 under blue LED irradiation with subsequent one-pot condensation with ammonium acetate. Based on cyclic voltammetry studies, it was determined that α,α-difluoro-β-iodoketones are reduced notably easier compared to 2,2,2-trifluoro-1-iodoethane, which may be ascribed to the influence of the carbonyl group. © 2017 American Chemical Society.