Hoover, Andrew J.Lazari, MarkRen, HongNarayanam, Maruthi KumarMurphy, Jennifer M.van Dam, R. MichaelHooker, JacobRitter, Tobias2016-05-022016Hoover, Andrew J., Mark Lazari, Hong Ren, Maruthi Kumar Narayanam, Jennifer M. Murphy, R. Michael van Dam, Jacob M. Hooker, and Tobias Ritter. 2016. “A Transmetalation Reaction Enables the Synthesis of [18F]5-Fluorouracil from [18F]Fluoride for Human PET Imaging.” Organometallics 35 (7): 1008-1014. doi:10.1021/acs.organomet.6b00059. http://dx.doi.org/10.1021/acs.organomet.6b00059.0276-7333http://nrs.harvard.edu/urn-3:HUL.InstRepos:26860130Translation of new 18F-fluorination reactions to produce radiotracers for human positron emission tomography (PET) imaging is rare because the chemistry must have useful scope and the process for 18F-labeled tracer production must be robust and simple to execute. The application of transition metal mediators has enabled impactful 18F-fluorination methods, but to date none of these reactions have been applied to produce a human-injectable PET tracer. In this article we present chemistry and process innovations that culminate in the first production from [18F]fluoride of human doses of [18F]5-fluorouracil, a PET tracer for cancer imaging in humans. The first preparation of nickel σ-aryl complexes by transmetalation from arylboronic acids or esters was developed and enabled the synthesis of the [18F]5-fluorouracil precursor. Routine production of >10 mCi doses of [18F]5-fluorouracil was accomplished with a new instrument for azeotrope-free [18F]fluoride concentration in a process that leverages the tolerance of water in nickel-mediated 18F-fluorination.en-USArticleJournal Article2016-05-0210.1021/acs.organomet.6b00059