AI Article Synopsis
- The study introduces a new method for selectively adding aryl groups to the meta position of phenols, overcoming the challenges of traditional synthetic routes.
- The method utilizes a unique strategy involving carbon dioxide as a temporary directing group to enable palladium-catalyzed reactions.
- This one-pot process shows complete meta-selectivity and works well with various functional groups in both the phenol and iodoarene reactants.
Article Abstract
The direct functionalization of phenols at the ortho and para position is generally facilitated by the electron-donating nature of the hydroxyl group. Accessing meta-functionalized phenols from the parent phenols, on the other hand, generally requires lengthy synthetic sequences. Here, we report the first methodology for the one-pot direct meta-selective arylation of phenols. This methodology is based on a traceless directing group relay strategy. In this process carbon dioxide is used as a transient directing group which facilitates a palladium catalyzed arylation meta to the phenol hydroxyl group with iodoarenes. This transformation proceeds with complete meta-selectivity and is compatible with a variety of functional groups both in the phenol and in the iodoarene coupling partner.
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| http://dx.doi.org/10.1021/ja500457s | DOI Listing |
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