通过电子给体-受体（EDA）配合物实现三芳基胺的全氟烷基化以及后续敏化的[6π]电环化反应合成全氟烷基化内型咔唑。机理与光物理研究
Perfluoroalkylation of Triarylamines by EDA Complexes and Ulterior Sensitized [6π]-Electrocyclization to Perfluoroalkylated Endo-Carbazoles. Mechanistic and Photophysical Studies.
作者信息
Romero Ivan E, Barata-Vallejo Sebastian, Bonesi Sergio M, Postigo Al
机构信息
Departamento de Ciencias Químicas, CONICET-Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junin 954, Buenos Aires, CP 1113, Argentina.
Departamento de Química Orgánica Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires Ciudad Universitaria, Buenos Aires, C1428EGA, Argentina.
出版信息
Chemistry. 2024 May 28;30(30):e202400905. doi: 10.1002/chem.202400905. Epub 2024 Apr 17.
Blue LEDs-irradiation of a mixture of N,N,N',N'-tetramethylethylenediamine (TMEDA) and perfluoroalkyl iodides (R-I) - Electron Donor Acceptor (EDA)-complex - in the presence of triphenylamines (TPAs) in an aqueous solvent mixture afforded mono-perfluoroalkylated triphenylamines (R-TPA) in good yields. These R-TPA were further subjected to acetone-sensitized [6π]-electrocyclization at 315 nm-irradiation affording exclusively perfluoroalkylated endo-carbazole derivatives (R-CBz) in quantitative yields. Mechanistic studies and photophysical properties of products are studied.
在水性溶剂混合物中，在三苯胺（TPA）存在的情况下，用蓝色发光二极管照射N，N，N'，N'-四甲基乙二胺（TMEDA）和全氟烷基碘（R-I）的混合物——电子给体-受体（EDA）络合物——以良好的产率得到单全氟烷基化三苯胺（R-TPA）。这些R-TPA在315 nm照射下进一步进行丙酮敏化的[6π]电环化反应，以定量产率专一性地得到全氟烷基化内型咔唑衍生物（R-CBz）。对产物的机理研究和光物理性质进行了研究。
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