Iodoephedrine reduction

[Lucid_Dreamer]

~"But what amalgum and I are pondering is reducing Iodoephedrine by other means than HI"~

DOH!

[Rhodium]

I can only think of HI(aq), PI₃, (CH₃)₃Si-I and possibly PPh₃/I₂ as being viable iodination reagents.

NaBH₄ in diglyme (yes, only in that solvent) will also reduce iodides to the hydrocarbon.

Selective Reductions. XI. The Reaction of Sodium Borohydride with Alkyl Halides under Solvolytic Conditions.
Harold M. Bell and Herbert C. Brown

J. Am. Chem. Soc. 88, 1473-1477 (1966)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/nabh4-diglyme.dehalogenation.pdf)

Abstract
In nonionizing solvents, secondary and tertiary alkyl halides react with sodium borohydride only slowly, in many cases yielding the olefin, rather than the desired saturated hydrocarbon. However, the addition of water to produce typical solvolyzing conditions brings about a rapid reaction, providing the corresponding hydrocarbon in good yield, along with the concomitant formation of the alcohol and the olefin as the usual solvolytic products. Evidence is presented which indicates that the mechanism of the reduction involves the trapping of the intermediate carbonium ions formed in the solvolysis. Consequently, the reaction should be useful, both synthetically, to convert reactive alkyl halides and their derivatives to the corresponding hydrocarbons, and mechanistically, to trap carbonium ions in investigations of their nature. A number of synthetic applications is described.

[Lucid_Dreamer]

That reminds me of the article on phosphorous trichloride breaking down in to h3po3 in water, the other one seems complex and makes me feel like a neanderthal.

Now pph3 and iodine, is that just another way to produce HI? or does it stand apart from the others?
Can you tell me what halogenation I might bee looking for Rhodium, side chain, alpha chain or whatever? Pretty please?

[Rhodium]

The reaction would be classified as a Iodination (halogenation) of a (secondary | benzylic) alcohol