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

Chinese Chemical Letters 2021年第4期32卷 1419-1422页

作者： Luxia Guo Zihao Chen Hongmei Zhu Minghao Li Yanlong Gu Huazhong University of Science and Technology Hubei Key Laboratory of Material Chemistry and Service FailureWuhan 430074China State Key Laboratory for Oxo Synthesis and Selective Oxidation Lanzhou Institute of Chemical PhysicsLanzhou 730000China The Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan Shihezi UniversityShihezi 832004China

chemodivergent reactions of 2,2-dimethoxyacetaldehyde and anilines were described,which were established on the basis of either a C—C bond cleavage or a rearrangement process of a reaction inte *** reactions proceeded in a condition-determined manner with good functional group *** the first model,2,2-dimethoxyacetaldehyde reacted with aniline to form a new C—N bond,in the presence of O_(2),via a C—C bond cleavage ***,in the second model,by performing the reaction in the absence of O_(2),Heyns rearrangement occurred and generated a new C—O bond to form methyl *** condition-determined reactions not only offered the new way for valueadded conversion of biomass-derived platform molecule,2,2-dimethoxyacetaldehyde,but also provided efficient methods for the synthesis of N-arylformamides and methyl phenylglycinates.

关键词： Condition-determined reaction chemodivergent reaction 2 2-Dimethoxyacetaldehyde C-C bond cleavage Heyns rearrangement

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Catalytic chemodivergent annulations betweenα-diketones and alkynylα-diketones

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Science China Chemistry 2021年第6期64卷 991-998页

作者： Xiangwen Kong Fang Yu Zhizhou Chen Fan Gong Shuang Yang Jinggong Liu Benlong Luo Xinqiang Fang State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of MatterUniversity of Chinese Academy of SciencesFuzhou 350100China Key Laboratory of Coal to Ethylene Glycol and Its Related Technology Center for Excellence in Molecular SynthesisFujian Institute of Research on the Structure of MatterUniversity of Chinese Academy of SciencesFuzhou 350100China Orthopedics Department Guangdong Provincial Hospital of Traditional Chinese MedicineThe Second Affiliated Hospital of Guangzhou University of Chinese MedicineGuangzhou 510120China Pingxiang University Pingxiang 337055China

Four types of unprecedented and chemodivergent reactions betweenα-diketones and alkynylα-diketones have been achieved under the catalysis of phosphine and Br?nsted base,respectively,leading to the rapid construction of four different classes of biologically important but synthetically challenging molecular scaffolds including 2-hydroxyfuran-3(2H)-ones,4-hydroxy-2-oxabicyclo[2.2.1]heptan-3-ones,1,3-diaryl cyclobutanes,and 4-(furan-2(3H)-ylidene)*** formation of the products includes two novel rearrangement processes,and further transformations on the products can be easily achieved to deliver value-added substances such as highly functionalized ***,the 2-hydroxyfuran-3(2H)-one products display promising photophysical properties such as green luminescence under UV light and aggregation-induced emission effect,showing the practical application value of this *** great potential ofα-diketones in both synthetic chemistry and material science has been unambiguously demonstrated.

关键词： chemodivergent reaction cascade annulation phosphine catalysis rearrangement reaction fluorescent material

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