Citation: Bo Li, Shihao Liu, Wu Fan, Xiaotong Shen, Jing Xu, Suhua Li. Ligand enabled none-oxidative decarbonylation of aliphatic aldehydes[J]. Chinese Chemical Letters, ;2023, 34(7): 108027. doi: 10.1016/j.cclet.2022.108027 shu

Ligand enabled none-oxidative decarbonylation of aliphatic aldehydes

Bo Li ^a ,
Shihao Liu ^a ,
Wu Fan ^b ,
Xiaotong Shen ^a ,
Jing Xu ^a ,
Suhua Li ^{a, *,}

a.
School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, China
b.
Key Laboratory of Tobacco Flavor Basic Research, Zhengzhou Tobacco Research Institute of CNTC, Zhengzhou 450001, China

lisuhua5@mail.sysu.edu.cn

Received Date: 31 August 2022
Revised Date: 22 November 2022
Accepted Date: 28 November 2022
Available Online: 29 November 2022

Figures(7)

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.
- Decarbonylation,
- Aliphatic aldehydes,
- Rhodium,
- Iridium,
- Ligand
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沈阳化工大学材料科学与工程学院沈阳 110142