Mechanism of Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen

development of a base-catalyzed iododeboronation for radiolabeling applications

John J. Molloy, Kerry M. O'rourke, Carolina P. Frias, Nikki L. Sloan, Matthew J. West, Sally L. Pimlott, Andrew Sutherland, Allan J.B. Watson

Research output: Contribution to journalArticle

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Abstract

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.
Original languageEnglish
Pages (from-to)2488-2492
Number of pages5
JournalOrganic Letters
Volume21
Issue number7
Early online date25 Mar 2019
DOIs
Publication statusPublished - 5 Apr 2019

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Lewis Bases
Boronic Acids
Lewis base
Halogens
Single-Photon Emission-Computed Tomography
Catalysis
halogens
catalysis
reagents
Substitution reactions
substitutes
preparation
acids
products

Keywords

  • boronic acid
  • halodeboronation
  • fluorodeboronation

Cite this

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. / Mechanism of Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen : development of a base-catalyzed iododeboronation for radiolabeling applications. In: Organic Letters. 2019 ; Vol. 21, No. 7. pp. 2488-2492.
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Mechanism of Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen : development of a base-catalyzed iododeboronation for radiolabeling applications. / 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.

In: Organic Letters, Vol. 21, No. 7, 05.04.2019, p. 2488-2492.

Research output: Contribution to journalArticle

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