Mechanism of Cu-Catalyzed Aryl Boronic Acid Halodeboronation Using Electrophilic Halogen: Development of a Base-Catalyzed Iododeboronation for Radiolabeling Applications
| Autor: | Nikki L. Sloan, Kerry M. O'Rourke, Allan J. B. Watson, Sally L. Pimlott, Andrew Sutherland, Matthew J West, Carolina P. Frias, John J. Molloy |
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| Přispěvatelé: | University of St Andrews. School of Chemistry, University of St Andrews. EaSTCHEM |
| Rok vydání: | 2019 |
| Předmět: |
inorganic chemicals
010405 organic chemistry Chemistry Aryl Organic Chemistry NDAS QD Chemistry 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Catalysis Turn (biochemistry) chemistry.chemical_compound Reagent Halogen Electrophile QD Lewis acids and bases Physical and Theoretical Chemistry Boronic acid |
| Zdroj: | Organic Letters. 21:2488-2492 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.9b00942 |
| Popis: | The authors are grateful to EPSRC (EP/R511705/1 and a studentship to K.M.O., EP/K503058/1) and the University of Glasgow. We thank the University of St Andrews (M.J.W) and CAPES/Science Without Borders (C.P.F) for PhD studentships. An investigation into the mechanism of Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen reagents is reported. Evidence is provided to show that this takes place via a boronate-driven ipso-substitution pathway and that Cu is not required for these processes to operate: general Lewis base catalysis is operational. This in turn allows the rational development of a general, simple, and effective base-catalyzed halodeboronation that is amenable to the preparation of 125I-labeled products for SPECT applications. Publisher PDF |
| Databáze: | OpenAIRE |
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