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Ligand enabled none-oxidative decarbonylation of aliphatic aldehydes

Chinese Chemical Letters 2023年第7期34卷 107-111页

作者： Bo Li Shihao Liu Wu Fan Xiaotong Shen Jing Xu Suhua Li School of Chemistry Sun Yat-Sen UniversityGuangzhou 510275China Key Laboratory of Tobacco Flavor Basic Research Zhengzhou Tobaco Research Institute of CNTCZhengzhou 450001China

Decarbonylation of aldehydes is a basic organic transformation, which has been developed for more than six-decade. However, as comparing to well-studied aromatic aldehydes, fewer examples for catalytic decarbonylation of aliphatic aldehydes were reported, mainly on simple or special *** α-bulky or highly functionalized ones, stoichiometric Rh(I) were usually required for decent ***, we present a rare example of Ir(I)-catalyzed direct decarbonylation of α-quaternary aldehydes with broad substrate scope and good functional group compatibility via judicious selection of ligand. Theα-chirality is memorized in this decarbonylation process. In addition, we report a broad-spectrum decarbonylation of α-secondary and α-tertiary aldehydes containing multifunctional groups with an improved Rh(I)/DPPP recipe. Finally, we realized selective decarbonylation of α-tertiary aldehydes in the presence of α-quaternary one via the reactivity differences.

关键词： Decarbonylation aliphatic aldehydes Rhodium Iridium Ligand

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A Novel Synthetic Method for the Preparation of aliphatic aldehydes from the Corresponding Carboxylic Acids

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Chinese Journal of Chemistry 2011年第3期29卷 489-492页

作者： Guo, Yuan Lu, Zhenhuan Yao, Libo Shi, Zhen Department of Biochemistry and Molecular Biology The Fourth Military Medical University Xi'an Shaanxi 710032 China College of Chemistry and Materials Science Northwest University Xi'an Shaanxi 710069 China

A novel synthetic method for the preparation of aliphatic aldehydes from the corresponding carboxylic acids via 1,3-dimethylbenzimidazolium salts is provided. 1,3-Dimethylbenzimidazolium salts were rapidly reduced with sodium/ethanol and then hydrolyzed with hydrochloric acid to obtain aliphatic aldehydes, in which the 1,3-dimethylbenzimidazolium salts can be readily achieved from the corresponding carboxylic acids. The mechanism for the reductive reaction of 1,3-dimethylbenzimidazolium salts with sodium/ethanol was discussed.

关键词： aliphatic aldehydes 1,3-dimethylbenzimidazolium salts reduction sodium synthetic method

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