1
$\begingroup$

We've been asked for the mechanism for the synthesis of the following difuran from the starting materials shown below:

enter image description here

The ytterbium complex will act as a Lewis acid and activate the oxygen of the benzaldehyde. However, I don't know what the next step in the mechanism would be.

$\endgroup$
  • 3
    $\begingroup$ Electrophilic aromatic substitution? $\endgroup$ – Zhe Oct 25 '16 at 21:31
6
$\begingroup$

This is actually a series of two electrophilic aromatic substitutions. The ytterbium stabilizes the benzyl cation enough for it to attack position 5 of the 2-methylfuran. After the new ytterbium complex dissociates away, the resulting cation can then attack another 2-methylfuran, and the final product is formed.

mechanism

$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.