Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 1, Pages 26-30Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201501405
Keywords
Manganese; C-H functionalization; Heterocycles; Cyclopropanols; Dual role reagent
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Funding
- National Science Foundation (NSF) [CHE 1152996, CHE 1465131]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1465131] Funding Source: National Science Foundation
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We report a direct C-H to C-C bond functionalization of electron-deficient heteroaromatics enabled by mild C-C bond cleavage of cyclopropanols as a new route to -aryl carbonyl-containing products. Additionally, as an alternative to using a catalyst that requires an excess amount of a sacrificial oxidant for regeneration and/or oxidative aromatization, this paper features manganese(IV) oxide as an inexpensive dual role reagent - effecting both C-C bond cleavage and ultimate rearomatization. Under the specified conditions, a variety of heterocycles proved competent for regioselective C-C bond formation, alongside a diverse array of cyclopropanols with broad functional-group tolerance. We highlight applications to complex-molecule synthesis and direct derivatization of biologically active alkaloids. Furthermore, kinetic isotope effect (KIE) experiments, radical scavengers, and some insight into the application of tri- and tetravalent manganese species are invoked to shape an initial mechanistic hypothesis.
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