Mechanism of Cu-catalyzed aryl boronic acid halode-boronation using electrophilic halogen : development of a base-catalyzed Iododeboronation for radiolabeling applications
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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.
Molloy , J , O’Rourke , K , Frias , C , Sloan , N , West , M , Pimlott , S , Sutherland , A & Watson , A J B 2019 , ' Mechanism of Cu-catalyzed aryl boronic acid halode-boronation using electrophilic halogen : development of a base-catalyzed Iododeboronation for radiolabeling applications ' , Organic Letters , vol. 21 , no. 7 , pp. 2488-2492 . https://doi.org/10.1021/acs.orglett.9b00942
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DescriptionThe 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.
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