Citation: Luxia Guo, Zihao Chen, Hongmei Zhu, Minghao Li, Yanlong Gu. Acid-catalyzed chemodivergent reactions of 2, 2-dimethoxyacetaldehyde and anilines[J]. Chinese Chemical Letters, ;2021, 32(4): 1419-1422. doi: 10.1016/j.cclet.2020.10.033 shu

Acid-catalyzed chemodivergent reactions of 2, 2-dimethoxyacetaldehyde and anilines

Luxia Guo ^a ,
Zihao Chen ^a ,
Hongmei Zhu ^a ,
Minghao Li ^{a, *,} ,
Yanlong Gu ^{a, b, c, *,}

a.
Huazhong University of Science and Technology, Hubei Key Laboratory of Material Chemistry and Service Failure, Wuhan 430074, China
b.
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Lanzhou 730000, China
c.
The Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi 832004, China

liminghaochem@hust.edu.cn

klgyl@hust.edu.cn

Received Date: 6 August 2020
Revised Date: 20 October 2020
Accepted Date: 21 October 2020
Available Online: 22 October 2020

Figures(4)

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.
- Condition-determined reaction,
- Chemodivergent reaction,
- 2, 2-Dimethoxyacetaldehyde,
- C—C bond cleavage,
- Heyns rearrangement
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