锌粉促进羰基化合物与卤代烃的碳碳键形成反应分析-analysis of zinc powder promoting carbon-carbon bond formation reaction between carbonyl compounds and halogenated hydrocarbons.docx

Abstract  PAGE 6 development of green chemistry and zinc powder mediated green organic synthesis research, we first time report olefination, silyetherization, etherization and Prins-cyclization were carried out from aromatic carbonyl compounds with aryl or alkyl halides using the Lewis acid (TMSiX) as regular mediated by zinc powder in one-pot under solvent-free conditions. Thirty-four (E)-alkene compounds, nine sily ethers, seven symmetry ethers and seven 2,4,6-trisubstituted tetrahydropyrans were synthesized using this procedure and thirty-one compounds are novel products. All products were characterized by melting point, IR, 1H NMR, 13C NMR, MS and elemental analyses, and we also investigated mechanism for these reaction. Base on the thesis experimental, We found the reaction that zinc powder mediated stereoselective olefination, silyetherization, etherization of carbonyl compounds with aryl or alkyl halide using the Lewis acid (TMSiX) as regular in one-pot under solvent-free conditions, and zinc-copper couple promoted Prins-cyclization of carbonyl compounds with aryl or alkyl halide in one-pot under solvent-free conditions. This new method offers the possibility for the formation of new C=C, C-O, O-Si bonds and the synthesis of the natural active products. At the same time, we began to focus on the different affects of varies factors on the carbonyl olefination, silyetherization, etherization and Prins-cyclization reactions were studied to afford the optimized reaction condition, and we propose the general reaction mechanism. Compared with literature methods, the valuable features of our methodology include: higher yield, shorter reaction time, broader substrate scope, good steroeselecivity and predictability, solvent-free and so on. The method accorded with green chemistry theory and illustrated friendly environment principle. Moreover, We also reported Reformatsky-Aldol reaction that zinc-copper couple promoted aldehydes carbonyl compounds with α-