Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 43, Pages 17207-17216Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja203576p
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Funding
- National Science Foundation Center for Stereoselective C-H Functionalization (CSCHF)
- NSF [CHE-0553581]
- Cherry Emerson Center for Scientific Computation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0958205] Funding Source: National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0943980] Funding Source: National Science Foundation
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The mixed-valent paddlewheel complex tetrakis-(2-oxypyridinato)diruthenium(II,III) chloride, [Ru-2(hp)(4)Cl], catalyzes intramolecular allylic C-H amination with bis-(homoallylic) sulfamate esters. These results stand in marked contrast to reactions performed with dirhodium catalysts, which favor aziridine products. The following discussion constitutes the first report of C-H amination using complexes such as [Ru-2(hp)(4)Cl] and related diruthenium adducts. Computational and experimental studies implicate a mechanism for [Ru-2(hp)(4)Cl]-promoted C-H amination involving hydrogen-atom abstraction/radical recombination and the intermediacy of a discrete, albeit short-lived, diradical species. The collective data offer a coherent model for understanding the preference of this catalyst to oxidize allylic (and benzylic) C-H bonds.
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