Journal
SCIENTIFIC REPORTS
Volume 7, Issue -, Pages -Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/s41598-017-17116-4
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Funding
- JSPS KAKENHI [24229011, 25460016]
- Asahi Glass Foundation
- Nagase Science Technology Development Foundation
- Yamada Science Foundation
- Sumitomo Foundation
- Grants-in-Aid for Scientific Research [25460016, 17H03017, 16K15097, 17H05430, 17H06173] Funding Source: KAKEN
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The iodoform reaction has long been used as a qualitative test for acetyl and/or ethanol units in organic molecules. However, its synthetic applications are quite limited. Here, we describe a tuned iodoform reaction for oxidative demethylation reaction with I-2 and t-BuOK in t-BuOH, in which in situ-generated t-BuOI serves as the chemoselective iodinating agent. This system enables one-step conversion of levulinic acid to succinic acid, a major four-carbon chemical feedstock. This oxidative demethylation is also applicable to other compounds containing an acetyl group/ethanol unit, affording the corresponding carboxylic acids in a selective manner.
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