Mechanism of Cu-catalyzed aryl boronic acid halode-boronation using electrophilic halogen: development of a base-catalyzed Iododeboronation for radiolabeling applications

John Molloy; Kerry O’Rourke; Carolina Frias; Nikki Sloan; Matthew West; Sally Pimlott; Andrew Sutherland; Allan J. B. Watson

doi:10.1021/acs.orglett.9b00942

Mechanism of Cu-catalyzed aryl boronic acid halode-boronation using electrophilic halogen: development of a base-catalyzed Iododeboronation for radiolabeling applications

John Molloy, Kerry O’Rourke, Carolina Frias, Nikki Sloan, Matthew West, Sally Pimlott, Andrew Sutherland, Allan J. B. Watson

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	2488-2492
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	7
Early online date	25 Mar 2019
DOIs	https://doi.org/10.1021/acs.orglett.9b00942
Publication status	Published - 5 Apr 2019

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10.1021/acs.orglett.9b00942Licence: CC BY

Molloy_2019_PL_Radiolabeling_CC
Copyright © 2019 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
Final published version, 1.98 MBLicence: CC BY

Cite this

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title = "Mechanism of Cu-catalyzed aryl boronic acid halode-boronation using electrophilic halogen: development of a base-catalyzed Iododeboronation for radiolabeling applications",

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.",

author = "John Molloy and Kerry O{\textquoteright}Rourke and Carolina Frias and Nikki Sloan and Matthew West and Sally Pimlott and Andrew Sutherland and Watson, \{Allan J. B.\}",

note = "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.",

year = "2019",

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doi = "10.1021/acs.orglett.9b00942",

language = "English",

volume = "21",

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journal = "Organic Letters",

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T1 - Mechanism of Cu-catalyzed aryl boronic acid halode-boronation using electrophilic halogen

T2 - development of a base-catalyzed Iododeboronation for radiolabeling applications

AU - Molloy, John

AU - O’Rourke, Kerry

AU - Frias, Carolina

AU - Sloan, Nikki

AU - West, Matthew

AU - Pimlott, Sally

AU - Sutherland, Andrew

AU - Watson, Allan J. B.

N1 - 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.

PY - 2019/4/5

Y1 - 2019/4/5

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85063948504

U2 - 10.1021/acs.orglett.9b00942

DO - 10.1021/acs.orglett.9b00942

M3 - Article

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JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

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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Methods for C-C and C-N bond formation using earth-abundant metals

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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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Methods for C-C and C-N bond formation using earth-abundant metals

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