New finding of the Chan-Lam coupling

Copper catalyzed boronic acids and OH or NH containing reaction is called Chan-Lam reaction. The reaction often perform in mild conditions under oxygen atmosphere.
Yes I have used the reaction to synthesize my target compound. But always yield was moderate and depends on steric effect.
Today I found useful article that is reported by researchers from Pfizer and Scripps research institute.
https://pubs.acs.org/doi/abs/10.1021/acs.joc.7b03100

They focused on cyclopropylation of phenols and azaheterocycles. Because cylopropyl group is very important and unique substituent for Medicinal Chemistry but sometime has difficulty to introduce. So new methodologies are required still now.

At first they optimized the reaction condition for O-cyclopropylation of phenols.
In table1 they found good condition with bidentate ligand and it gave high yield (84%). Next they investigated scope and limitation of the reaction.
It was interesting for me that the condition give high yield against not only para substituted electron rich phenol but also ortho substituted phenols.
And also the condition gave low – moderate yield against para meta substituted electron poor phenols.
Procedure of the reaction is not so complicate. I would like to try to use the reaction if I have chance. Organic synthesis and medicinal chemistry is fun and creative task I think.

BTW, I think that introduction of cyclopropan MMP sounds like sudden.

Advertisement

Published by iwatobipen

I'm medicinal chemist in mid size of pharmaceutical company. I love chemoinfo, cording, organic synthesis, my family.

2 thoughts on “New finding of the Chan-Lam coupling

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.

%d bloggers like this: