- Redox-Neutral Organometallic Elementary Steps at Bismuth: Catalytic Synthesis of Aryl Sulfonyl Fluorides
-
A Bi-catalyzed synthesis of sulfonyl fluorides from the corresponding (hetero)aryl boronic acids is presented. We demonstrate that the organobismuth(III) catalysts bearing a bis-aryl sulfone ligand backbone revolve through different canonical organometallic steps within the catalytic cycle without modifying the oxidation state. All steps have been validated, including the catalytic insertion of SO2 into Bi-C bonds, leading to a structurally unique O-bound bismuth sulfinate complex. The catalytic protocol affords excellent yields for a wide range of aryl and heteroaryl boronic acids, displaying a wide functional group tolerance.
- Cornella, Josep,Magre, Marc
-
supporting information
p. 21497 - 21502
(2022/01/03)
-
- An in situ combinatorial methodology to synthesize and screen chemical probes
-
Chemical probes that label proteins of interest in the context of complex biological samples are useful research tools. The reactive group that forms the covalent bond with the target protein has a large effect on the selectivity and selecting the appropriate group determines the success of a probe. We here report the development of a combinatorial methodology based on imine chemistry that enables straightforward in situ synthesis and screening of different reactive groups and thereby simplifies identification of probe leads. Using our methodology, we found chemical probes targeting BirA and chloramphenicol acetyl transferase, two proteins associated with antibacterial activity and resistance.
- Van Der Zouwen, Antonie J.,Lohse, Jonas,Wieske, Lianne H. E.,Hohmann, Katharina F.,Van Der Vlag, Ramon,Witte, Martin D.
-
supporting information
p. 2050 - 2053
(2019/02/19)
-
- Ascertaining the suitability of aryl sulfonyl fluorides for [18F]radiochemistry applications: A systematic investigation using microfluidics
-
Optimization of [18F]radiolabeling conditions and subsequent stability analysis in mobile phase, PBS buffer, and rat serum of 12 aryl sulfonyl chloride precursors with various substituents (electron-withdrawing groups, electron-donating groups, increased steric bulk, heterocyclic) were performed using an Advion NanoTek Microfluidic Synthesis System. A comparison of radiochemical yields and reaction times for a microfluidics device versus a conventional reaction vessel is reported. [18F]Radiolabeling of sulfonyl chlorides in the presence of competing nucleophiles, H-bond donors, and water was also assessed and demonstrated the versatility and potential utility of [18F]sulfonyl fluorides as synthons for indirect radiolabeling. Published 2013 by the American Chemical Society.
- Matesic, Lidia,Wyatt, Naomi A.,Fraser, Benjamin H.,Roberts, Maxine P.,Pham, Tien Q.,Greguric, Ivan
-
p. 11262 - 11270
(2013/12/04)
-
- Sulfonyl fluoride-based prosthetic compounds as potential 18F labelling agents
-
Nucleophilic incorporation of [18F]F- under aqueous conditions holds several advantages in radiopharmaceutical development, especially with the advent of complex biological pharmacophores. Sulfonyl fluorides can be prepared in water
- Inkster, James A. H.,Liu, Kate,Ait-Mohand, Samia,Schaffer, Paul,Guérin, Brigitte,Ruth, Thomas J.,Storr, Tim
-
supporting information; experimental part
p. 11079 - 11087
(2012/09/22)
-