A General Direct Aldehyde C–H Alkylation via TBADT-Nickel Synergistic Catalysis
Herein, we present a nickel/tetrabutylammonium decatungstate (TBADT)-catalyzed protocol for general C-H alkylation of aldehydes, enabling the efficient synthesis of aliphatic ketones through ligand-controlled cross-coupling. This mild and cost-effective methodology demonstrates broad substrate compatibility with various commercially available aldehydes and both activated and unactivated alkyl bromides, delivering target products in high yields. Notably, the practical utility of this catalytic system has been highlighted through a concise two-step synthesis of the commercially valuable musk odorant Aurelione from readily available starting materials.
Authors
- Qiuhao Li
- Ji‐Wei Sang
- Zheng‐Yang Xu (ORCID: https://orcid.org/0000-0003-4605-8286)
- Yonghua Song (ORCID: https://orcid.org/0000-0002-1495-4644)
- Zhimin Hu (ORCID: https://orcid.org/0000-0002-9360-1686)
- Jinxin Wang (ORCID: https://orcid.org/0000-0001-9561-7633)
- Bing Wang (ORCID: https://orcid.org/0000-0003-4945-7725)
- Weidong Zhang (ORCID: https://orcid.org/0000-0003-3633-0581)
- Yu Zhang (ORCID: https://orcid.org/0000-0002-7230-3575)
- Runhui Liu (ORCID: https://orcid.org/0000-0001-7489-4957)
- Shuhua Xie (ORCID: https://orcid.org/0009-0002-8500-2023)
Institutions
- Second Military Medical University (CN)
- Wenzhou Medical University (CN)
- Institute of Organic Chemistry with Centre of Phytochemistry (BG)
- Integrative Medicine Institute (US)
- Central Research Laboratories (United Kingdom) (GB)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-25
- DOI
- https://doi.org/10.1021/acs.orglett.5c00949
- Citations
- 4
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 3.74
Funders
- National Natural Science Foundation of China
- Science and Technology Commission of Shanghai Municipality