The Article related to tetrasubstituted arene preparation regioselective transition state structure dft, aryl mesyl iodonium tosylate aryne arylation, substituent effect linear free energy relationship regioselectivity aryne formation, arylation, aryne, deprotonation, diaryliodonium salt, hypervalent iodine and other aspects.Synthetic Route of 321-28-8
On April 28, 2021, Nilova, Aleksandra; Sibbald, Paul A.; Valente, Edward J.; Gonzalez-Montiel, Gisela A.; Richardson, H. Camille; Brown, Kevin S.; Cheong, Paul Ha-Yeon; Stuart, David R. published an article.Synthetic Route of 321-28-8 The title of the article was Regioselective Synthesis of 1,2,3,4-Tetrasubstituted Arenes by Vicinal Functionalization of Arynes Derived from Aryl(Mes)iodonium Salts. And the article contained the following:
Herein, the synthesis of 1,2,3,4-tetrasubstituted benzenoid rings, motifs found in pharmaceutical, agrochem., and natural products, is described. In the past, the regioselective syntheses of such compounds have been a significant challenge. This work reports a method using substituted arynes derived from aryl(Mes)iodonium salts to access a range of densely functionalized 1,2,3,4-tetrasubstituted benzenoid rings. Significantly, it was found that halide substituents are compatible under these conditions, enabling post-synthetic elaboration via palladium-catalyzed coupling. This concise strategy is predicated on two regioselective events: 1) ortho-deprotonation of aryl(Mes)iodonium salts to generate a substituted aryne intermediate, and 2) regioselective trapping of said arynes, thereby improving previously reported reaction conditions to generate arynes at room temperature and in shorter reaction times. D. functional theory (DFT) computations and linear free energy relationship (LFER) anal. suggest the regioselectivity of deprotonation is influenced by both proximal and distal ring substituents on the aryne precursor. A competition experiment further reveals the role of arene substituents on relative reactivity of aryl(Mes)iodoniums as aryne precursors. The experimental process involved the reaction of 1-Fluoro-2-methoxybenzene(cas: 321-28-8).Synthetic Route of 321-28-8
The Article related to tetrasubstituted arene preparation regioselective transition state structure dft, aryl mesyl iodonium tosylate aryne arylation, substituent effect linear free energy relationship regioselectivity aryne formation, arylation, aryne, deprotonation, diaryliodonium salt, hypervalent iodine and other aspects.Synthetic Route of 321-28-8
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