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The Diaryliodonium(III) Salts Reaction With Free-Radicals Enables One-Pot Double Arylation of Naphthols
Frontiers in Chemistry ( IF 5.5 ) Pub Date : 2020-08-17 , DOI: 10.3389/fchem.2020.563470
Yuvraj Satkar , Kazimierz Wrobel , Daniel E. Trujillo-González , Rafael Ortiz-Alvarado , J. Oscar C. Jiménez-Halla , César R. Solorio-Alvarado

The chemoselective reaction of the C- followed by the O-centered naphthyl radicals with the more electron-deficient hypervalent bond of the diaryliodonium(III) salts is described. This discovered reactivity constitutes a new activation mode of the diaryliodonium(III) salts which enabled a one-pot doubly arylation of naphthols through the sequential Csp2-Csp2/O-Csp2 bond formation. The naphthyl radicals were generated in the reaction by the tetramethylpiperidinyl radical (TMP·) which resulted from the homolytic fragmentation of the precursor TMP2O. Experimental and DFT calculations provided a complete panorama of the reaction mechanism.



中文翻译:

与自由基的二芳基碘鎓(III)盐反应可实现萘酚的一锅双芳基化

的化学选择性反应 C-其次 O-描述了具有中心电子的二芳基碘鎓(III)盐具有更高电子缺陷的高价键的萘基。这一发现的反应性构成了二芳基碘鎓盐的一种新的活化模式,从而可以通过顺序使一锅的萘酚双芳基化Csp2--Csp2/ O-Csp2键的形成。萘基自由基是由四甲基哌啶基自由基(TMP·)在反应中生成的,四甲基哌啶基自由基是由前体TMP 2 O的均相裂解产生的。实验和DFT计算提供了反应机理的完整概图。

更新日期:2020-10-16
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