Decarboxylative Acetoxylation of Aliphatic Carboxylic Acids

Article abstract of DOI:10.1021/acs.joc.9b02092

Organic molecules bearing acetoxy moieties are important functionalities in natural products, drugs, and agricultural chemicals. Synthesis of such molecules via transition metal-catalyzed C-O bond formation can be achieved in the presence of a carefully chosen directing group to alleviate the challenges associated with regioselectivity. An alternative approach is to use ubiquitous carboxylic acids as starting materials and perform a decarboxylative coupling. Herein, we report conditions for a photocatalytic decarboxylative C-O bond formation reaction that provides rapid and facile access to the corresponding acetoxylated products. Mechanistic investigations suggest that the reaction operates via oxidation of the carboxylate followed by rapid decarboxylation and oxidation by Cu(OAc)₂

Full text of DOI:10.1021/acs.joc.9b02092

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Article
Decarboxylative Acetoxylation of Aliphatic Carboxylic Acids
Sameera Senaweera, Kaitie C. Cartwright, and Jon A Tunge
J. Org. Chem., Just Accepted Manuscript • DOI: 10.1021/acs.joc.9b02092 • Publication Date (Web): 10 Sep 2019
Downloaded from pubs.acs.org on September 12, 2019
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ASSOCIATED CONTENT
Supporting Information
AUTHOR INFORMATION
Corresponding Author
Notes
ACKNOWLEDGMENT
.
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