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Synthesis 2023; 55(16): 2547-2553
DOI: 10.1055/a-2055-2313
DOI: 10.1055/a-2055-2313
paper
Pd-Catalyzed MIA-Directed Methoxylation of Phenylalanines: A Combined Experimental and Computational Study
We are grateful for the financial support from the National Natural Science Foundation of China (grant No. 21978124) and Key Projects of Ningbo Natural Science Foundation (grant No. 2022J003).
Abstract
The direct methoxylation of substituted phenylalanines has been accomplished via methoxyiminoacyl (MIA)-mediated Pd-catalyzed C–H functionalization. A diverse array of ortho-methoxylated phenylalanine derivatives are efficiently generated in good to high yields. KIE study has shown that the oxhydryl cleavage step is the rate-limiting step. The computational data show that the participation manner of methanol has a great influence on the energy barriers of transition states during the C(sp2)–O formation stage. The pathway containing stepwise deprotonation and reductive elimination is superior to that of a concerted deprotonation-methoxylation.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2055-2313.
- Supporting Information
Publication History
Received: 10 January 2023
Accepted after revision: 15 March 2023
Accepted Manuscript online:
15 March 2023
Article published online:
20 April 2023
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