[cdeewo]

Hi everyone,
Do you think that a Friedel Crafts acylation could be possible using a phenylboronic acid (or a phenylboronic ester such as pinacol ester) as the aromatic substrate? I haven't found anything in the literature, so I was wondering if there could be a reactivity issue.
Thanks!

[rolnor]

There is probably problem with mixing a boronic acid and the Lewis acid catalyst, the catalyst will react and hydrolyze. If you use a arylboronic acid ester it could work if you use a mixed acyl-trifluoromethanesulphonyl anhydride as acylating agent, this can be made from a acyl chloride and trifluoromethanesulphonic acid. I say it could work, boron is so special, hard to know how it will behave. One option can be to use a excess Lewis acid, again, it could work. A boronic derivative like this is a nucleophile and it can compete with the aromatic nucleus and attack the activated acylating agent.

[cdeewo]

Thanks for the thoughts rolnor! I guess we'll give it a shot and see....