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Tetrabutylammonium Iodide (TBAI) Catalyzed Electrochemical C–H Bond Activation of 2-Arylated N-Methoxyamides for the Synthesis of Phenanthridinones
Synlett ( IF 1.7 ) Pub Date : 2021-03-25 , DOI: 10.1055/a-1467-5585
Bhalchandra M. Bhanage , Kripa Subramanian , Subhash L. Yedage , Kashish Sethi

An electrochemical method for the synthesis of phenanthridinones through constant-potential electrolysis (CPE) mediated by Bu4NI (TBAI) is reported. The protocol is metal and oxidant free, and proceeds with 100% current efficiency. TBAI plays a dual role as both a redox catalyst and a supporting electrolyte. The intramolecular C–H activation proceeds under mild reaction conditions and with a short reaction time through electrochemically generated amidyl radicals. The reaction has been scaled up to a gram level, showing its practicability, and the synthetic utility and applicability of the protocol have been demonstrated by a direct one-step synthesis of the bioactive compound phenaglaydon.

中文翻译:

四丁基碘化碘(TBAI)催化2-丙烯酸N-甲氧基酰胺的电化学C–H键活化,用于合成菲啶酮

报道了一种通过Bu4NI(TBAI)介导的恒电位电解(CPE)合成菲咯烷酮的电化学方法。该协议不含金属和氧化剂,并且以100%的电流效率进行。TBAI既起着氧化还原催化剂的作用,又起支持电解质的作用。分子内C–H活化是在温和的反应条件下并通过电化学生成的酰胺基在较短的反应时间内进行的。该反应已按比例放大至克级,显示出其实用性,并且该协议的合成效用和适用性已通过生物活性化合物苯乙酰胺的直接一步合成来证明。
更新日期:2021-04-09
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