bleh another one of those _Organic Syntheses_ entries where you look at it and think "welp I probably ain't never gonna even think of using this one"
the reaction: oxidative coupling of aryltrialkylsilanes to electron-rich arenes to yield unsymmetrical biaryls. high-valent iodine reagents as the oxidizing agent, in the presence of racemic camphorsulfonic acid (camphorsulfonic acid?! why?) and *gold* catalysis
I kinda wanna play with the hypervalent iodine stuff but only with polymer-bound versions. that would offer an easy way to recover and reuse the precious iodine
it's totally a thing. here's a randomly chosen Google Images result for polymer-bound IBX ("IBX" is the usual abbreviation for "iodoxybenzoic acid" which is really a benziodoxole derived from oxidation of 2-iodobenzoic acid)
what's the point of this? hypervalent iodine reagents are one of the few types of chemical reagent that can be made to carry out organic oxidations that traditionally require heavy metals (like hexavalent chromium or osmic acid). and they can be regenerated after use with auxiliary oxidizers that are cheap and clean, like peroxo salts
jeez kinda wonder if hypervalent iron can be a thing. like, people have tried to use inorganic "ferrates" (hexavalent iron salts with the FeO4= anion) as oxidants
are there organoiron(6) compounds?
huh. decamethylferrocene can be oxidized to Fe(4). wonder if that's any use for anything
ooh here's a thing! porphyrin complexes of iron(4) that can achieve certain organic oxidations
I feel like a synthesis like this, in an earlier age of _Organic Syntheses_, would have had a lot more trials done on whether you really needed the weird reagents. there'd be footnotes about how they'd tried (say) methanesulfonic acid or toluenesulfonic acid instead of camphorsulfonic acid, only with poorer results. we'd get more glimpses into the experimental process