Three-Component Direct Phosphorylation of Aldehydes and Alkylation of Ketones: Synthesis of γ-Ketophosphine Oxides under Acidic Conditions
Xiao-Hong Wang, Ya-Wen Xue, Chun-Yuan Bai, Yan-Bin Wang, Xiao-Hong Wei*, Qiong Su*
*College of Chemical Engineering, Northwest Minzu University,
Lanzhou 730030, P. R. China, Email: weixh12
lzu.edu.cn, hgsqxbmu.edu.cn
X.-H. Wang, Y.-W. Xue, C.-Y. Bai, Y.-B. Wang, X.-H. Wei, Q. Su, J. Org. Chem., 2023, 88, 16216-16228.
DOI: 10.1021/acs.joc.3c01674
see article for more reactions
Abstract
An effective and economical acid-promoted three-component reaction enables the construction of C-P and C-C bonds for the synthesis of γ-ketophosphine oxides with water as the only byproduct. The reaction proceeds by phospha-aldol elimination, in which a benzylic carbocation is generated from the phosphorylation of aldehydes, which then reacts with ketone enolates under acidic conditions.
see article for more examples
proposed mechanism
Key Words
multicomponent reactions, phosphine oxides
ID: J42-Y2023
