Meta-Selective Alkylation of Phenolic Substrates

The technology is a method of meta-selective alkylation which requires no heating and has short reaction times relative to existing processes. The process relies on dearomatization of phenolic rings, introduction of the functional group at the meta- position, and rearomatization of the phenol. The process requires no directing group.

Background:

The inventors have created a detailed procedure for the process and have applied it to a range of phenolic substrates.

Applications:

• The process can be applied in research as a way to cut costs and time requirements for necessary alkylation procedures. Because the process is relatively inexpensive it might also open research avenues that were prohibited by cost before.
• Since the process may replace more complex, multistep syntheses, industrial-scale manufacturing could benefit from a more easily automated, cheaper, faster procedure.

Advantages:

• No directing group; many meta-selective arylation processes require large, complex, potentially expenisve directing groups. These add expense and further steps to the process. This process does not require a directing group.
• No transition metal catalysts; many other processes require expensive transition metal catalysts. This process does not.
• Fast, no heating required; almost all other processes require long (20-48 hour) reaction periods at high temperatures (50-500° C). This process requires no heating and could plausibly be completed in one day.
• Functional group tolerance; many processes are limited to certain functional groups (commonly aryl groups). This process is not so limited and is demonstrated with alkyl groups.