Journal
ORGANIC LETTERS
Volume 13, Issue 8, Pages 2071-2073Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol200441g
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Funding
- Ara Parseghian Medical Research Foundation
- University of Notre Dame College of Science
- American Chemical Society
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A practical, chemoselective oxidation of alcohols employing catalytic quantities of DDQ as the oxidant and Mn(OAc)(3) as the co-oxidant is described. Electron-rich benzylic alcohols are oxidized efficiently to their corresponding carbonyls, but less electron-rich benzylic alcohols remain unchanged. Allylic alcohols are rapidly oxidized to their corresponding aldehyde or ketone counterparts in high yields. This protocol is operationally simple, employs an inexpensive source of Mn(OAc)(3), has short reaction times, and exhibits a significant chemoselectivity favoring allylic alcohols over benzylic alcohols. This procedure also avoids the use of very large excesses of reagents and sometimes poor reproducibility that characterize previously developed reagents such as MnO2.
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