Abstract
AbstractOrganoboron compounds are well known building blocks for many organic reactions. However, under basic conditions, polyfluorinated aryl boronic acid derivatives suffer from instability issues that are accelerated in compounds containing an ortho‐fluorine group, which result in the formation of the corresponding protodeboronation products. Therefore, a considerable amount of research has focused on novel methodologies to synthesize these valuable compounds while avoiding the protodeboronation issue. This review summarizes the latest developments in the synthesis of fluorinated aryl boronic acid derivatives and their applications in cross‐coupling reactions and other transformations.magnified image
Highlights
In this review we summarize the latest developments regarding the synthesis of fluorinated aryl boronate derivatives, discuss the stability issue of these molecules, and highlight the latest developments in the applications of fluorinated aryl boronates in organic synthesis
Selectivities observed in platinum-catalyzed CÀ H reactions reported by Iwasawa[36] and Tobisu and Chatani[39] were dictated by electronic effects, whereupon the most acidic arene CÀ H bonds ortho to the fluorine groups underwent borylation
As naturally occurring sources of aryl fluorides have not yet been identified, this class of molecules must be generated through chemical synthesis
Summary
Interest in fluorinated organic compounds has increased in recent years as these remarkable compounds have a vast array of important applications, including but not limited to, material science, pharmaceutical and agricultural chemistry, specialty chemical industries, and catalysis. Udo Radius received his Diploma and Ph.D. from the University of Würzburg For his Ph.D. he worked with Helmut Werner and Jörg Sundermeyer on organometallic chemistry of group 6 transition metals in high oxidation states. Following postdoctoral research at the University of Bristol in England, he spent two years as a Visiting Research Scientist at DuPont Central Research in Wilmington He joined the faculty at the University of Waterloo, Canada in 1985, and in 1995 was awarded the Rutherford Memorial Medal for Chemistry of the Royal Society of Canada. Marder’s diverse research interests include synthesis, structure, bonding and reactivity of organometallic and metalÀ boron compounds, homogeneous catalysis, small molecule triggers of stem cell differentiation, luminescence, nonlinear optics, bioimaging, liquid crystals, and crystal engineering. In this review we summarize the latest developments regarding the synthesis of fluorinated aryl boronate derivatives, discuss the stability issue of these molecules, and highlight the latest developments in the applications of fluorinated aryl boronates in organic synthesis
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