Ligand enabled none-oxidative decarbonylation of aliphatic aldehydes |
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| Institution: | 1. School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, China;2. Key Laboratory of Tobacco Flavor Basic Research, Zhengzhou Tobacco Research Institute of CNTC, Zhengzhou 450001, China;1. Cancer Institute (Key Laboratory of Cancer Prevention and Intervention, China National Ministry of Education), The Second Affiliated Hospital, Zhejiang University School of Medicine, Hangzhou 310009, China;2. Cancer Center, Zhejiang University, Hangzhou 310058, China;1. Department of Environmental Science and Engineering, Xi''an Jiaotong University, Xi''an 710049, China;2. Research Institute of Xi''an Jiaotong University, Hangzhou 311200, China;1. Department of Dermatology, the Second Hospital Affiliated to Xi''an Jiaotong University, Xi''an 710061, China;2. School of Chemical Engineering and Technology, Xi''an Jiaotong University, Xi''an 710049, China;3. Infectious Disease Department, the Second Xiangya Hospital of Central South University, Changsha 410011, China;4. Pooling Medical Research Institutes, Hangzhou 310053, China;5. Department of Pharmacy, Shaanxi Provincial People''s Hospital, Xi''an 710068, China;1. Department of Chemistry, Jinan University, Guangzhou 510632, China;2. Department of Orthopedics, Affiliated Hospital of Guangdong Medical University, Zhanjiang 524001, China;1. State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, College of Life Sciences and KLMDASR of Tianjin, Nankai University, Tianjin 300353, China;2. School of Chemistry, Tiangong University, Tianjin 300387, China |
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| Abstract: | 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 substrates. For α-bulky or highly functionalized ones, stoichiometric Rh(I) were usually required for decent yields. Herein, 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. The α-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. |
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