Grignard Reagent‐Mediated Regioselective 1,8‐Addition of α‐(2‐Thienylidene)‐β‐ketosulfones

Grignard reagent‐mediated and solvent‐controlled regioselective 1,8‐addition of α‐(2‐thienylidene)‐β‐ketosulfones provides diversified substituted 2‐thienylmethyl β‐ketosulfones in moderate yields in a diethyl ether–dioxane cosolvent and dioxane (v/v=4/1) under ice‐bath conditions. The 1,4‐addition...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2023-07, Vol.365 (13), p.2264-2270
Main Authors: Chang, Meng‐Yang, Chen, Kuan‐Ting, Chen, Hsing‐Yin
Format: Article
Language:English
Subjects:
Addition
Bromides
Cosolvent
C−H Functionalization
Diethyl ether
Reagents
Regioselectity
Regioselectivity
Solvents
Transition metals
β-Ketosulfone
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Summary:Grignard reagent‐mediated and solvent‐controlled regioselective 1,8‐addition of α‐(2‐thienylidene)‐β‐ketosulfones provides diversified substituted 2‐thienylmethyl β‐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 α‐heterocyclic β‐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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300227