Mechanism of Cu-Catalyzed Aryl Boronic Acid Halodeboronation Using Electrophilic Halogen: Development of a Base-Catalyzed Iododeboronation for Radiolabeling Applications

Mechanism of Cu-Catalyzed Aryl Boronic Acid Halodeboronation Using Electrophilic Halogen: Development of a Base-Catalyzed Iododeboronation for Radiolabeling Applications

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: gene...

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Veröffentlicht in:Organic letters 2019-04, Vol.21 (7), p.2488-2492
Hauptverfasser: Molloy, John J, O’Rourke, Kerry M, Frias, Carolina P, Sloan, Nikki L, West, Matthew J, Pimlott, Sally L, Sutherland, Andrew, Watson, Allan J. B
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container_end_page 2492
container_issue 7
container_start_page 2488
container_title Organic letters
container_volume 21
creator Molloy, John J
O’Rourke, Kerry M
Frias, Carolina P
Sloan, Nikki L
West, Matthew J
Pimlott, Sally L
Sutherland, Andrew
Watson, Allan J. B
description 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.
doi_str_mv 10.1021/acs.orglett.9b00942
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title Mechanism of Cu-Catalyzed Aryl Boronic Acid Halodeboronation Using Electrophilic Halogen: Development of a Base-Catalyzed Iododeboronation for Radiolabeling Applications
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