期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 365, 期 13, 页码 2264-2270出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202300227
关键词
Addition; beta-Ketosulfone; Regioselectity; C-H Functionalization; Cosolvent
In this study, a diverse range of substituted 2-thienylmethyl beta-ketosulfones were synthesized through a Grignard reagent-mediated and solvent-controlled 1,8-addition reaction. The reaction was conducted in a diethyl ether-dioxane cosolvent and dioxane (v/v=4/1) under ice-bath conditions, resulting in moderate yields. Additionally, the 1,4-addition reaction of alpha-heterocyclic beta-ketosulfones was also investigated, and the structure of the key product was confirmed using X-ray analysis. DFT calculations were employed to rationalize the regioselectivity of the 1,8-addition reaction.
Grignard reagent-mediated and solventcontrolled regioselective 1,8-addition of alpha-(2-thienylidene)-beta-ketosulfones provides diversified substituted 2-thienylmethyl beta-ketosulfones in moderate yields in a diethyl ether-dioxane cosolvent and dioxane (v/v= 4/1) under ice-bath conditions. The 1,4-addition of alpha-heterocyclic beta-ketosulfones was also studied. The structure of the key product was confirmed via X-ray analysis. The uses of various reaction solvents and organomagnesium bromides were investigated for transition metal-free C H functionalization. Related plausible mechanisms are proposed and discussed. The DFT calculations are utilized to rationalize the regioselectivity of the 1,8-addition reaction.
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