[Baerchen]

Hi!
I am trying to do a lithium exchange with an allylic iodide. Does anyone have some practical tips to help out as so far I cannot get the reaction to occur.

I have been hammering the lithium then dipping it in MeOH then X4 before chucking it in the flask with a bit of dry ether. I've tried refluxing the mixture and sonication but nothing happens.

I have been able to form the organolithium with tBuLi but it's so reactive I am getting the Wurtz coupling product despite trying cooler temps, more and less equivs of tBuLi. That's why I think the lithium metal would be the way to go - if I can initiate the rn!

Thank you in advance

[408]

Try adding lithium chloride in addition to the Li metal.

[stewie griffin]

Have you tried sec-BuLi or looked at the conditions Knochel uses (he uses LiCl alot... as 408 suggests). Maybe just make the Grignard?