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Full-Text Articles in Physical Sciences and Mathematics
An Efficient And Chemoselective Method To Generate Arynes, Bryan Metze, Riley A. Roberts, Aleksandra Nilova, David R. Stuart
An Efficient And Chemoselective Method To Generate Arynes, Bryan Metze, Riley A. Roberts, Aleksandra Nilova, David R. Stuart
Chemistry Faculty Publications and Presentations
Arynes hold immense potential as reactive intermediates in organic synthesis as they engage in a diverse range of mechanistically distinct chemical reactions. However, the poor functional group compatibility of generating arynes or their precursors has stymied their widespread use. Here, we show that generating arynes by deprotonation of an arene and elimination of an “onium” leaving group is mild, efficient and broad in scope. This is achieved by using aryl(TMP)iodonium salts (TMP = 2,4,6-trimethoxyphenyl) as the aryne precursor and potassium phosphate as the base, and a range of arynophiles are compatible. Additionally, we have performed the first quantitative analysis of …
Studies On Bonding, Syntheses, And Applications Of Diarylhalonium Compounds, Shubhendu Karandikar
Studies On Bonding, Syntheses, And Applications Of Diarylhalonium Compounds, Shubhendu Karandikar
Dissertations and Theses
Organic compounds containing functionalized benzenoid rings have found tremendous applications in pharmaceuticals, agrochemicals, commodity chemicals, and beyond. As a result, development of methods for the synthesis of functionalized benzenoid rings has gained much attention from the synthetic community. Although many transition-metal mediated methods to functionalize benzenoid rings are known, there has been an upsurge of activity in developing protocols for decoration of benzenoid cores promoted by p-block elements. This excitement stems from the sustainability of earth-abundant elements and unique reactivity patterns observed within the p-block. Among these, transformations promoted by hypervalent halogen compounds, and especially, the diarylhalonium salts are very …