Universidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Departamento de Química Orgánica, Junín 954, CP1113-Buenos Aires, Argentina.
Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Pabellón 2, Ciudad Universitaria, C1428EG Buenos Aires, Argentina.
Org Biomol Chem. 2020 Nov 4;18(42):8724-8734. doi: 10.1039/d0ob01914c.
A benign, efficient, regio- and stereoselective protocol for the syntheses of α-1-fluoroalkyl-C-glycosyl compounds bearing CF3, C4F9, and C6F13 substituents on the anomeric carbon has been developed by a new methodology starting from 2-acetoxyglycals for the first time. Remarkably, the reactions proceeded in only one step, through the visible light-photocatalyzed reductive fluoroalkylation of 2-acetoxyglycals by means of an Ir photocatalyst and employed commercially available fluoroalkyl iodides n-CnF2n+1-I (n = 1, 4, 6) as a source of fluoroalkyl radicals.
首次开发出一种新颖的方法，通过可见光光催化还原氟烷基化反应，以 Ir 光催化剂为催化剂，使用商业可得的氟烷基碘化物 n-CnF2n+1-I（n = 1、4、6）作为氟烷基自由基的来源，从 2-乙酰基糖苷出发，首次为在α-1-氟烷基-C-糖苷化合物的合成中构建 CF3、C4F9 和 C6F13 取代基的区域和立体选择性的温和、高效方法。值得注意的是，反应仅通过一步即可进行。
