Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: yonkim on May 22, 2006, 11:50:51 AM
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In the attached hyperlink there's a description of Reformatzky Reaction with variation: An iodolactone is coupled with an aldehyde with triethylborane.
http://en.wikipedia.org/wiki/Image:Reformatskii_Danishefsky_2006.png
What does the mechanism look like?
I have a seminar tomorrow, so I would really appreciate your kind assistance!
Thanks.
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Heh, I saw Danishefsky talk about this very chemistry last year! It was done by a post-doc in his lab who used to be a grad student at my school. Another grad student who recently graduated from my lab is now working on some chemistry closely related to this particular reaction, also as a post-doc in the Danishefsky lab.
As for the mechanism, although I don't think it is completely understood, this is almost certainly a radical reaction at some level. It is known that triethylborane can serve as a radical initiator, usually after exposure to a small amount of oxygen. The initiator probably then reacts with the iodine to generate a radical alpha to the carbonyl group which can then pick up another electron at generate a boron enolate. This enolate subsequently adds in to the aldehyde.
Here is a link to the paper:
http://pubs3.acs.org/acs/journals/doilookup?in_doi=10.1021/ja0574567