Facile pinacol coupling of aliphatic ketones by Brook rearrangement in the presence of samarium species
Autor: | Xiaoxia Wang, Xincan Wang, Ke Zheng, Yanfei Zhao, Guanqun Xie, Yanxiong Fang |
---|---|
Rok vydání: | 2021 |
Předmět: |
Aromatic ketone
Pinacol coupling reaction Silylation 010405 organic chemistry Pinacol Organic Chemistry Diol chemistry.chemical_element Brook rearrangement 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Samarium Coupling (electronics) chemistry.chemical_compound chemistry Drug Discovery |
Zdroj: | Tetrahedron Letters. 72:153069 |
ISSN: | 0040-4039 |
Popis: | Herein we report a practical pinacol coupling reaction, in which ketones (aldehydes) react smoothly with Sm and TMSBr to afford the diol products with Sm(II) or (III) siliyl species generated in situ. This reported method affords poor yields for aromatic ketone substrates and good yields for aliphatic ketones. Therefore, it distinguishes from most reductive coupling approaches that are more effective for aromatic carbonyl compounds and provides a facile and robust approach for the pinacol coupling of aliphatic ketones. Mechanistic studies also indicated the pinacolization probably proceeded via an anionic instead of radical coupling pathway involving the Brook rearrangement in the presence of samarium (II or III) silyl species. |
Databáze: | OpenAIRE |
Externí odkaz: |