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. 2025 Jun 6;90(22):7507-7509.
doi: 10.1021/acs.joc.5c00476. Epub 2025 May 27.

Protective Group-Dependent Iridium-Catalyzed CH Borylations of Levodopa

Cliff Yang  1 , Jinda Fan  1   2   3 , Robert E Maleczka Jr  1
Affiliations

Protective Group-Dependent Iridium-Catalyzed CH Borylations of Levodopa

Cliff Yang et al. J Org Chem. .

Abstract

Despite being an important aromatic amino acid, iridium-catalyzed borylation (CHB) of levodopa has not been reported. Via the application of carefully chosen protecting groups for the catechol moiety, the steric hindrance around the arene can be reduced, enabling selective C5 CHB of levodopa. Methylene and boronic ester protecting groups were explored, the latter of which is deprotected in situ to yield the free catechol.

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Figures

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1
Derivatives of levodopa with traditional protecting groups for the catechol moiety.
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1. Iridium-Catalyzed Borylation of Levodopa Derivatives Including the Benzodioxole Moiety
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2. Post Borylation Functionalization of Levodopa
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3. Borylation of a Levodopa Derivative Protected by Boronic Acid to Yield the Deprotected Catechol
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