Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 42, Pages 15742-15745Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja409241h
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Funding
- DOE [DE-FG02-05ER15690]
- NSF [CHE-9208463]
- NIH [S10 RR08389]
- ACS GCI Pharmaceutical Roundtable
- Eli Lilly
- Pfizer
- Merck
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1048642] Funding Source: National Science Foundation
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Cu/TEMPO catalyst systems promote efficient aerobic oxidation of sterically unhindered primary alcohols and electronically activated substrates, but they show reduced reactivity with aliphatic and secondary alcohols. Here, we report a catalyst system, consisting of ((MeO)bpy)Cu-I(OTf) and ABNO ((MeO)bpy = 4,4'-dimethoxy-2,2'-bipyridine; ABNO = 9-azabicyclo[3.3.1]nonane N-oxyl), that mediates aerobic oxidation of all classes of alcohols, including primary and secondary allylic, benzylic, and aliphatic alcohols with nearly equal efficiency. The catalyst exhibits broad functional group compatibility, and most reactions are complete within 1 h at room temperature using ambient air as the source of oxidant.
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