155204-26-5Relevant articles and documents
The use of lithium amides in the palladium-mediated synthesis of [carbonyl-11C]amides
Itsenko, Oleksiy,Blom, Elisabeth,Langstroem, Bengt,Kihlberg, Tor
, p. 4337 - 4342 (2007)
Weakly nucleophilic amines were converted into the corresponding lithium amides and used in either one- or two-pot palladium-mediated reactions with [11C]carbon monoxide and aryl iodides. It was found that palladium acyl complexes may be prepared in a separate step and have sufficient life-time to be used in a subsequent reaction with a nucleophile. This two-pot procedure was used for the labelling synthesis of eleven amides (nine of which are analogues of WAY-100635, a 5-HT1A radioligand) from weakly nucleophilic amines. The results were compared to a direct one-pot procedure using lithium amides. Both approaches extend the scope of palladium-mediated carbonylation using [11C]carbon monoxide and aryl iodides allowing use of weakly nucleophilic amines. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Nucleophilic deoxyfluorination of phenols via aryl fluorosulfonate intermediates
Schimler, Sydonie D.,Cismesia, Megan A.,Hanley, Patrick S.,Froese, Robert D.J.,Jansma, Matthew J.,Bland, Douglas C.,Sanford, Melanie S.
supporting information, p. 1452 - 1455 (2017/02/10)
This report describes a method for the deoxyfluorination of phenols with sulfuryl fluoride (SO2F2) and tetramethylammonium fluoride (NMe4F) via aryl fluorosulfonate (ArOFs) intermediates. We first demonstrate that the reaction of ArOFs with NMe4F proceeds under mild conditions (often at room temperature) to afford a broad range of electronically diverse and functional group-rich aryl fluoride products. This transformation was then translated to a one-pot conversion of phenols to aryl fluorides using the combination of SO2F2 and NMe4F. Ab initio calculations suggest that carbon-fluorine bond formation proceeds via a concerted transition state rather than a discrete Meisenheimer intermediate.
Synthesis of NCA [carbonyl-11C]-Labeled Amides Using a Polymer-Supported Carbodiimide under Microwave Conditions
Lu, S. Y.,McCarron, J. A.,Hong, J. S.,Musachio, J. L.,Pike, V. W.
, p. S229 - S229 (2007/10/03)
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