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Copper-Catalyzed Electrochemical Selective B-H Oxygenation of o-Carboranes at Room Temperature
Yik Ki Au1, Hairong Lyu1, Yangjian Quan1
1Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, N. T., Hong Kong, China.
Abstract:
Copper-catalyzed electrochemical selective cage B-H oxygenation of o-carboranes has been achieved for the first time. Under a constant electric current (4.0 mA) at room temperature, copper-catalyzed cross-coupling of carboranyl amides with lithium phenolates results in the formation of B(4,5)-diphenolated o-carboranes via direct B-H activation, whereas the use of lithium tert-butoxide affords B(4)-monooxygenated products. This reaction does not require any additional chemical oxidants and generates H2 and a lithium salt as byproducts. Control experiments indicated that a high-valent Cu(III) species is likely involved in the reaction process.
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