Selective Metal-Controlled Synthesis of Trifluoromethylated (Indolin-2-ylidene)methyl- and Quinolin-3-ylphosphonates.,The Journal of Organic Chemistry

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Selective Metal-Controlled Synthesis of Trifluoromethylated (Indolin-2-ylidene)methyl- and Quinolin-3-ylphosphonates.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-06-22 , DOI: 10.1021/acs.joc.0c00913
Alexander Yu Mitrofanov ₁ , Valentina A Bychkova ₁ , Sergey E Nefedov ₂ , Irina P Beletskaya ₁

Affiliation

Metal-catalyzed (Cu, Ag, Au) reactions of alkynylphosphonates with 1-(2-aminophenyl)-2,2,2-trifluoroethan-1-ones were developed. Terminal alkyne diethyl ethynylphosphonate reacted with ketones to give different products depending on the catalyst used. With a CuI/PPh₃ catalytic system, the formation of CF₃-containing indoline derivatives was observed with good yields. The use of AgSbF₆ as a catalyst led to quinoline derivatives in high yields. The less reactive 2-substituted ethynylphosphonates required gold complexes as catalysts to provide the corresponding 2-aryl(alkyl) substituted 4-(trifluoromethyl)quinolin-3-ylphosphonates with good yields.

中文翻译：

三氟甲基化（吲哚-2-亚基）甲基和喹啉-3-基膦酸酯的选择性金属控制的合成。

开发了炔基膦酸酯与1-（2-氨基苯基）-2,2,2-三氟乙烷-1-酮的金属催化的（Cu，Ag，Au）反应。末端炔基二乙基乙炔基膦酸酯与酮反应生成不同的产物，具体取决于所使用的催化剂。用CuI / PPh ₃催化体系，观察到以良好的产率形成了含CF ₃的二氢吲哚衍生物。使用AgSbF ₆作为催化剂可以高产率生产喹啉衍生物。反应性较低的2-取代的乙炔基膦酸酯需要金配合物作为催化剂，以提供具有良好收率的相应的2-芳基（烷基）取代的4-（三氟甲基）喹啉-3-基膦酸酯。

更新日期：2020-06-22

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