期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 19, 页码 12553-12561出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02092
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资金
- National Science Foundation [CHE-1800147]
- Kansas Bioscience Authority Rising Star program
- NSF Academic Research Infrastructure Grant [9512331]
- NIH Shared Instrumentation Grant [S10RR024664]
- NSF Major Research Instrumentation Grant [0320648]
- Direct For Biological Sciences
- Div Of Biological Infrastructure [9512331] Funding Source: National Science Foundation
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).
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