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Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes
Author(s) -
Webster Stacey,
O'Rourke Kerry M.,
Fletcher Conor,
Pimlott Sally L.,
Sutherland Andrew,
Lee AiLan
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704534
Subject(s) - radiosynthesis , chemistry , combinatorial chemistry , catalysis , solvent , pet imaging , radiochemistry , organic chemistry , nuclear medicine , positron emission tomography , medicine
Radiopharmaceuticals that incorporate radioactive iodine in combination with single‐photon emission computed tomography imaging play a key role in nuclear medicine, with applications in drug development and disease diagnosis. Despite this importance, there are relatively few general methods for the incorporation of radioiodine into small molecules. This work reports a rapid air‐ and moisture‐stable ipso ‐iododeboronation procedure that uses NIS in the non‐toxic, green solvent dimethyl carbonate. The fast reaction and mild conditions of the gold‐catalysed method led to the development of a highly efficient process for the radiolabelling of arenes, which constitutes the first example of an application of homogenous gold catalysis to selective radiosynthesis. This was exemplified by the efficient synthesis of radiolabelled meta ‐[ 125 I]iodobenzylguanidine, a radiopharmaceutical that is used for the imaging and therapy of human norepinephrine transporter‐expressing tumours.