84322-55-4Relevant academic research and scientific papers
Utilising Sodium-Mediated Ferration for Regioselective Functionalisation of Fluoroarenes via C?H and C?F Bond Activations
Maddock, Lewis C. H.,Nixon, Tracy,Kennedy, Alan R.,Probert, Michael R.,Clegg, William,Hevia, Eva
supporting information, p. 187 - 191 (2017/12/07)
Pairing iron bis(amide) Fe(HMDS)2 with Na(HMDS) to form new sodium ferrate base [(dioxane)0.5?NaFe(HMDS)3] (1) enables regioselective mono and di-ferration (via direct Fe?H exchange) of a wide range of fluoroaromatic substrates under mild reaction conditions. Trapping of several ferrated intermediates has provided key insight into how synchronised Na/Fe cooperation operates in these transformations. Furthermore, using excess 1 at 80 °C switches on a remarkable cascade process inducing the collective twofold C?H/threefold C?F bond activations, where each C?H bond is transformed to a C?Fe bond whereas each C?F bond is transformed into a C?N bond.
Generation of fluorinated m-benzyne derivatives in neon matrices
Wenk, Hans Henning,Sander, Wolfram
, p. 3927 - 3935 (2007/10/03)
The fluorinated m-didehydrobenzenes 5-H-, 5-deuterio-, 5-(trifluoromethyl)-, 5-(trimethylsilyl)-, and 5-iodo-2,4,6-trifluoro-1,3-didehydrobenzene 6b-6f were generated by UV photolysis of the corresponding 1,3-diiodobenzene derivatives 4b-4f in solid neon
Extensive halogen scrambling and buttressing effects encountered upon treatment of oligobromoarenes with bases
Mongin, Florence,Marzi, Elena,Schlosser, Manfred
, p. 2771 - 2777 (2007/10/03)
As a rule, tri-, tetra- and pentahaloarenes readily undergo ortho-lithiation when treated with amide-type bases. However, halogen migration occurs whenever the substrate contains three or more contiguous halogen atoms, provided that at least one of them is bromine or iodine. Dismutation and reduction processes often take place concomitantly. In this manner, a variety of organometallic intermediates may be formed, the driving force always being a decrease in basicity. When no such energy gain can be achieved, a sterically crowded substrate may just turn out to be inert; this was found to be the case with 1,5-dibromo-3-fluoro-2-(trimethylsilyl)benzene, 1,5-dibromo-3-fluoro-2,4-bis(trimethylsilyl)benzene, and 1,5-dibromo-3-fluoro-2,4-diiodobenzene. Buttressing effects are apparently strong enough to prevent expedient deprotonation of those substrates.
