Ye Olde One was browsing wikipedia earlier on, and came across the article on Stryker's reagent, interesting looking stuff, due to its apparent ease of synthesis (going from the wiki article, the supporting references he still needs)

Structure is  ([(PPh3)CuH]6, it is highly air sensitive, although can be stored, apparently, under an inert atmosphere without problems, and transferred quickly such as to a rxn vessel without significant decomposition, Stryker's complex is a selective reducing agent for carbonyl groups, the wiki article states that it is tolerant of multiple different C=O containing moieties.

Preparation wise, there are a couple of routes to it, the one detailed in wikipedia looks very feasible, practically speaking, and uses no hideously poisonous, nor highly expensive reagents (that said, having been quite probably been poisoned with PPH3 and/or its oxide...it was not a pleasant experience, one gets alarmed when coughing blood).

It appears to be a fairly simple synthesis, to quote from the wiki ''Stryker's reagent is prepared from copper(I) tert-butoxide, generated in situ from copper(I) chloride and sodium tert-butoxide, and pressurized hydrogen. It can be directly prepared from copper(II) salts as well.''

Presumably giving the hydride of copper, to be ligated with TPP.

What makes it look particularly attractive, is that it can be regenerated in-situ during a reduction, using either a silane, or better still, molecular H2, allowing for the use of catalytic amounts of the complex.

Nothing terribly difficult to obtain or prepare is used, and the triphenylphosphine should be recoverable, as its oxide precipitates out usually, given its poor solubility in many rxn solvents, such as light alkanes and ether. Reduction of that to PPH3 is possible. Although how worthwhile, in many cases, it would be if 'catalytic' quantities are used is debatable unless the reactions were to bee run on a large scale.



Anyone care to discuss?

Question, if anybody knows: whilst Stryker's reagent will reduce esters, aldehydes, ketones, enones and enals, will it reduce an amide to an amine? and can it be used for reductive amination of either a ketone or aldehyde? if so, it would look a lot nicer than mercury-based reductive amination routes for those who use Al/Hg amalgams for aminating (MDO)(meth)amphetamine P2Ps and the like.

Particularly interested in finding out weather it can be used for reducing amide carbonyls. If so, Toady sees quite a few pretty facile end products coming from melatonin+acyl halide, to give the appropriate 5-MeO-n-ethyl-n-alkyl subsituted tryptamines. 5-MeO-MET excluded, given the instability of formyl halides.

Lastly...
And would anyone be so good as to get hold of these reference, if they have access? Toady would have asked in the reference request thread, if it weren't for the fact that his memory issues are playing up very badly since just recently, and he is struggling to remember words, he won't remember having the need for the papers come an hour from now possibly, and come tomorrow..he would be surprised if he has remembered.

Direct synthesis of Stryker's reagent from Cu(II) salt". Tetrahedron Lett. 46 (12): 2037–2039. doi:10.1016/j.tetlet.2005.01.127

Preparation and crystallographic characterization of a hexameric triphenylphosphinecopper hydride cluster

J. Am. Chem. Soc., 1971, 93 (, pp 2063–2065
DOI: 10.1021/ja00737a045

J. Am. Chem. Soc., 1988, 110 (1), pp 291–293
DOI: 10.1021/ja00209a048

Thanks wizard X.

Although no sooner does Tsathoggua order half a kilo of TPP that was going cheap....his blasted memory problem leads him to forget what he was wanting to investigate Stryker's reagent for in the first place.

Hopefully it might come to him in the end, but not likely, going on how his memory issues have screwed things up in the past.

He will figure something to do with it though, one way or the other.

And typically, as usual when he sets his beady amphibian eyes on THAT auction site, other things follow. Hydrazine, a new hotplate/mag stirrer, another thermometer adapter which comes with a thermometer going up to 330'C, 50, 100, 150, 250 and 500ml 1-neck RBFs, 100 and 250ml 2-neck RBFs, 100&250ml 3-neck RB flasks, another liebig condenser, and various vacuum adapters, distillation receivers, claisen adapters....

Toady is awful...terrible bugger he is for lab shopping, once he goes looking for some needed supplies, you can just bet that following close behind his purchase will be twenty more.

His microscope came today in the mail...40-2000x. He is positively itching to get the chance to use it. Thankfully the indian seller agreed to mark it as 'commercial sample, no business transaction involved' and save ye olde toad god from the filthy grasping clutches of those verminous, thieving customs&excise scum

He dare not even think about looking at the selection of stains currently on offer, for fear that he will be too tempted to buy stains for everything conceivably possible he might encounter and leave him having to eat nothing but bread, cheese and scraps for the next month again.

Such is his terrible acquisition habit, that he is converting the room next to his sleeping quarters into a second lab   All he set out to buy was half a kilo of triphenylphosphine, but he ended up spending close to £450:P

Although he DOES need to get the stains needed to perform a Gomori trichrome stain, to check for the possibility of a mitochondrial disorder