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 rmediate.These reactio...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 rmediate.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 C—N bond,in the presence of O_(2),via a C—C bond cleavage reaction.However,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 phenylglycinate.Such 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.展开更多
基金the National Natural Science Foundation of China for financial support(Nos.2171101076,21872060 and 21902054)Fundamental Research Funds for the Central Universities(No.2019kfyXJJS072)Natural Science Foundation of Hubei Province(No.2019CFB219)。
文摘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 rmediate.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 C—N bond,in the presence of O_(2),via a C—C bond cleavage reaction.However,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 phenylglycinate.Such 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.
基金国家自然科学基金项目(42362023)陕西省教育厅青年创新团队项目(24JP217,22RCYPJB0103)+2 种基金榆林市青年科技新星项目(2024-KJZG-QNXX-007)陕西省科技厅项目(2025JC-YBQN-456,2025JC-YBMS-452)中国科学院洁净能源创新研究院-榆林学院联合基金项目(YLU-DNL Fund 2022012)。
