December 03, 2021, 03:09:25 PM
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Topic: example of catalytic iodide in nuclephilic catalysis  (Read 217 times)

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Offline Babcock_Hall

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example of catalytic iodide in nuclephilic catalysis
« on: September 22, 2021, 01:48:23 PM »
Does anyone have an example of this off the top of their heads?  I need it for pedagogical purposes, not for a particular synthetic problem. I thought I had seen an example, possibly in March's book, but I am coming up empty right now, and I do not recall the details.

I found one example on-line (which comes from Clayden's textbook) in which a catalytic amount of lithium iodide sped up the production of a phosphonium salt from benzyl bromide and PPh3 in refluxing xylene. This will probably suffice for my purposes, but other examples that anyone has on hand would also be welcome.
« Last Edit: September 22, 2021, 02:01:10 PM by Babcock_Hall »

Online rolnor

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Re: example of catalytic iodide in nuclephilic catalysis
« Reply #1 on: September 22, 2021, 04:35:45 PM »
Alkylation with alkyl chlorides and bromides are catalyzed generally by iodide.
I think also conversion of benzoic esters to benzoyl amides by amines are catalyzed by iodide. This reaction is also catalyzed by cyanide ion.

Offline wildfyr

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Re: example of catalytic iodide in nuclephilic catalysis
« Reply #2 on: September 22, 2021, 05:57:29 PM »
Ring opening of epoxides can be catalyzed with some iodide salts.

Online rolnor

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Re: example of catalytic iodide in nuclephilic catalysis
« Reply #3 on: September 25, 2021, 09:05:39 AM »
(Edit) I think it should be alkyl esters, not benzoic esters.

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