Acid-catalyzed chemodivergent reactions of 2,2-dimethoxyacetaldehyde and anilines |
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Authors: | Luxia Guo Zihao Chen Hongmei Zhu Minghao Li Yanlong Gu |
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Institution: | 1. Huazhong University of Science and Technology, Hubei Key Laboratory of Material Chemistry and Service Failure, Wuhan 430074, China;2. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Lanzhou 730000, China;3. The Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi 832004, China |
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Abstract: | Chemodivergent reactions of 2,2-dimethoxyacetaldehyde and anilines were described, which were established on the basis of either a CC bond cleavage or a rearrangement process of a reaction intermediate. These reactions proceeded in a condition-determined manner with good functional group tolerance. In the first model, 2,2-dimethoxyacetaldehyde reacted with aniline to form a new CN bond, in the presence of O2, via a CC bond cleavage reaction. However, in the second model, by performing the reaction in the absence of O2, Heyns rearrangement occurred and generated a new CO bond to form methyl phenylglycinate. Such condition-determined reactions not only offered the new way for value-added conversion of biomass-derived platform molecule, 2, 2-dimethoxyacetaldehyde, but also provided efficient methods for the synthesis of N-arylformamides and methyl phenylglycinates. |
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Keywords: | Condition-determined reaction Chemodivergent reaction 2 2-Dimethoxyacetaldehyde Heyns rearrangement |
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