Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 26, Pages 9797-9804Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja4026424
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Funding
- DOE [DE-FG02-05ER15690]
- National Science Foundation [CHE09-52054]
- University of Minnesota
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0952054] Funding Source: National Science Foundation
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Copper(II)-mediated C-H oxidation is the subject of extensive interest in synthetic chemistry, but the mechanisms of many of these reactions are poorly understood. Here, we observe different products from Cu-II-mediated oxidation of N-(8-quinolinyl)benzamide, depending on the reaction conditions. Under basic conditions, the benzamide group undergoes directed C-H methoxylation or chlorination. Under acidic conditions, the quinoline group undergoes nondirected chlorination. Experimental and computational mechanistic studies implicate an organometallic C-H activation/functionalization mechanism under the former conditions and a single-electron-transfer mechanism under the latter conditions. This rare observation of divergent, condition-dependent mechanisms for oxidation of a single substrate provides a valuable foundation for understanding Cu-II-mediated C-H oxidation reactions.
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