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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Spontaneous and Efficient Oxime Synthesis by Al-Catalyst Assembly
Shu-Lin Meng1,2, Wen-Jie Kang1,2, Chen-Ho Tung1,2
1Key Laboratory of Supramolecular Photochemistry & CAS-HKU Joint Laboratory on New Materials, New Cornerstone Science Laboratory, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, P. R. China.
None:
As an important category of organic nitrogenous compounds, oxime synthesis requires extensive energy input to fulfill multielectron transformation. Herein, we accomplish oxime synthesis via a spontaneous reaction for the first time under ambient conditions. By intimately assembling aluminum (Al) with a NOx- (x = 2, 3) reduction catalyst, the multielectron oxime synthesis proceeds with excellent yields, in which Al offers a strong driving force and high capacity for electron transfer, and CuZn alloy foil as an efficient catalyst presents extraordinary stability. Using abundant NOx- feedstocks, the C-N coupling is achieved to realize tandem, gram-scale air-to-oxime synthesis integrating plasma-driven N2 oxidation. Taking advantage of recycled Al resources, the oxime synthesis method demonstrates promising profitability and energy efficiency. The broad scope of aldehyde and ketone substrates enables successful oximation of bioactive and drug molecules, offering convenient access to utilize abundant resources for the synthesis of value-added nitrogenous compounds.
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