19169-99-4Relevant articles and documents
Remote Substituents as Potential Control Elements for the Solid-State Structures of Hypervalent Iodine(III) Compounds
Li, Guobi,Rheingold, Arnold L.,Protasiewicz, John D.
supporting information, p. 7865 - 7875 (2021/05/26)
Hypervalent iodine (HVI) compounds are very important selective oxidants often employed in organic syntheses. Most HVI compounds are strongly associated in the solid state involving interactions between the electropositive iodine centers and nearby electr
The Coming of Age in Iodane-Guided ortho-C?H Propargylation: From Insight to Synthetic Potential
Izquierdo, Susana,Bouvet, Sébastien,Wu, Yichen,Molina, Sonia,Shafir, Alexandr
supporting information, p. 15517 - 15521 (2018/10/02)
As early as 1991 Ochiai et al. reported that an acid-activated form of phenyliodine diacetate, PhI(OAc)2, undergoes a reaction with propargyl-silanes, germanes and stannanes to give the ortho-propargyl iodobenzene. This formal C?H alkylation wa
NH-Heterocyclic Aryliodonium Salts and their Selective Conversion into N1-Aryl-5-iodoimidazoles
Wu, Yichen,Izquierdo, Susana,Vidossich, Pietro,Lledós, Agustí,Shafir, Alexandr
supporting information, p. 7152 - 7156 (2016/07/06)
The synthesis of N-arylimidazoles substituted at the sterically encumbered 5-position is a challenge for modern synthetic approaches. A new family of imidazolyl aryliodonium salts is reported, which serve as a stepping stone on the way to selective formation of N1-aryl-5-iodoimidazoles. Iodine acts as a “universal” placeholder poised for replacement by aryl substituents. These new λ3-iodanes are produced by treating the NH-imidazole with ArI(OAc)2, and are converted to N1-aryl-5-iodoimidazoles by a selective copper-catalyzed aryl migration. The method tolerates a variety of aryl fragments and is also applicable to substituted imidazoles.
