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Bioorg Med Chem Lett. 2015 Apr 15;25(8):1761-1764. doi: 10.1016/j.bmcl.2015.02.055. Epub 2015 Mar 2.

Mild, Pd-catalyzed stannylation of radioiodination targets.

Author information

1
Molecular Pharmacology and Chemistry Program, Department of Neurology, Memorial Sloan Kettering Cancer Center, 1275 York Avenue, New York, NY 10065, USA.
2
Tri-Institutional Training Program in Chemical Biology, Memorial Sloan Kettering Cancer Center, 1275 York Avenue, Box 422, New York, NY 10065, USA.
3
Molecular Pharmacology and Chemistry Program, Department of Neurology, Memorial Sloan Kettering Cancer Center, 1275 York Avenue, New York, NY 10065, USA. Electronic address: majumdas@mskcc.org.

Abstract

Trialkylstannanes are versatile precursors for chemical transformations, including radiolabeling with a variety of halogens, particularly iodine. In the present work a convenient, Pd-mediated stannylation method is presented that can be performed in an open flask. The method is selective for aryl iodides allowing selective stannylations in the presence of other halogen atoms. The reaction conditions are mild, making the method compatible with chemically sensitive bioactive compounds.

KEYWORDS:

Opioid; Radioiodination; Radioligand binding; Sigma receptor; Stannylation

PMID:
25777268
PMCID:
PMC4385467
DOI:
10.1016/j.bmcl.2015.02.055
[Indexed for MEDLINE]
Free PMC Article

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