Front Cover: Borosilicate Activation of (Difluoroiodo)toluene in the gem-Difluorination of Phenyldiazoacetate Derivatives (Eur. J. Org. Chem. 27/2016)

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• 作者：Geoffrey S. Sinclair ; Richard Tran ; Jason Tao ; W. Scott Hopkins and Graham K. Murphy
• 刊名：European Journal of Organic Chemistry
• 出版年：2016
• 出版时间：September 2016
• 年：2016
• 卷：2016
• 期：27
• 页码：4586
• 全文大小：2987K
• ISSN：1099-0690

文摘

The cover picture shows the proposed sequence of events for the borosilicate glass-activated gem-difluorination of phenyl diazoacetate using the hypervalent iodine reagent (difluoroiodo)toluene (TolIF₂). Progress from diazo to gem-difluoride involves two distinct fluorination events and the evolution of nitrogen gas. Quantum chemical calculations of a borosilicate-like cluster show that the boron atom is sufficiently Lewis-acidic so as to spontaneously abstract fluoride from TolIF₂. The role of borosilicate glassware, which is the most effective activator discovered to date, was confirmed experimentally. Details are discussed in the Communication by W. S. Hopkins, G. K. Murphy et al. on p. 4603 ff.