2013
DOI: 10.1002/anie.201302800
|View full text |Cite
|
Sign up to set email alerts
|

Nickel‐Mediated Radioiodination of Aryl and Heteroaryl Bromides: Rapid Synthesis of Tracers for SPECT Imaging

Abstract: Rapid and efficient radioiodination of aryl and heteroaryl bromides has been achieved using a nickel(0)-mediated halogen-exchange reaction. This transformation gives direct access to [(123)I]- and [(125)I]-imaging agents for single photon emission computed tomography (SPECT), such as 5-[(123)I]-A85380 (see scheme, Boc = tert-butyloxycarbonyl, cod = 1,5-cyclooctadiene, TFA = trifluoroacetic acid).

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1
1

Citation Types

0
25
0
1

Year Published

2016
2016
2020
2020

Publication Types

Select...
7
2

Relationship

3
6

Authors

Journals

citations
Cited by 46 publications
(26 citation statements)
references
References 26 publications
0
25
0
1
Order By: Relevance
“…Moreover,t he reaction wast olerant of halogen moieties (Br and Cl), which is complementary to the commonly used halogen-exchange method to form aryl iodides. [33] The gold-catalysed iododeboronation reaction was shown to be ah ighly amenable procedure for the 125 I-labelling of arenes, which constitutes the first example of an application of homogenous gold catalysis to selectiver adiosynthesis. Under the optimised radiochemistry conditions, both electron-rich and electron-poor aryl boronic acids were rapidly convertedt ot he radioiodinated products in excellent RCY.T his general method was validated with the efficient synthesis and isolation of radioiodinated MIBG, at racer that is used for the imaging of cancer.C urrents tudies are ongoing to investigate the extension of this methodology for the preparation of existing and novel SPECT imaging agents.…”
Section: Discussionmentioning
confidence: 99%
“…Moreover,t he reaction wast olerant of halogen moieties (Br and Cl), which is complementary to the commonly used halogen-exchange method to form aryl iodides. [33] The gold-catalysed iododeboronation reaction was shown to be ah ighly amenable procedure for the 125 I-labelling of arenes, which constitutes the first example of an application of homogenous gold catalysis to selectiver adiosynthesis. Under the optimised radiochemistry conditions, both electron-rich and electron-poor aryl boronic acids were rapidly convertedt ot he radioiodinated products in excellent RCY.T his general method was validated with the efficient synthesis and isolation of radioiodinated MIBG, at racer that is used for the imaging of cancer.C urrents tudies are ongoing to investigate the extension of this methodology for the preparation of existing and novel SPECT imaging agents.…”
Section: Discussionmentioning
confidence: 99%
“…However, these reactions are often associated with issues related to low radiochemical yields (RCYs), low specific activities, or concerns about the toxicity of the precursors and side products when considering human use. Consequently, the development of novel methodologies to improve the radiolabeling of arenes with heavy halogens remains an active area of research …”
Section: Introductionmentioning
confidence: 99%
“…Consequently, the development of novel methodologies to improve the radiolabeling of arenes with heavy halogens remains an active area of research. [17,18] Compared to iodine, the chemistry of astatine remains largely unexplored despite more than 70 years since the discovery of this element. [19] Its chemical behavior is not well understood and can differ significantly from the trends observed with the other halogens.…”
Section: Introductionmentioning
confidence: 99%