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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| Published in | Advanced synthesis & catalysis Vol. 365; no. 13; pp. 2264 - 2270 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
04.07.2023
Wiley Subscription Services, Inc |
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| Abstract | 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. |
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| AbstractList | 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. 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. |
| Author | Chen, Hsing‐Yin Chang, Meng‐Yang Chen, Kuan‐Ting |
| Author_xml | – sequence: 1 givenname: Meng‐Yang orcidid: 0000-0002-1983-8570 surname: Chang fullname: Chang, Meng‐Yang email: mychang@kmu.edu.tw organization: National Pingtung University of Science and Technology – sequence: 2 givenname: Kuan‐Ting surname: Chen fullname: Chen, Kuan‐Ting organization: Kaohsiung Medical University – sequence: 3 givenname: Hsing‐Yin surname: Chen fullname: Chen, Hsing‐Yin email: hychen@kmu.edu.tw organization: Kaohsiung Medical University |
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| Keywords | SCHLENK EQUILIBRIUM Addition Cosolvent 1,6-CONJUGATE ADDITION beta-Ketosulfone ASYMMETRIC CONJUGATE ADDITION ORGANOCATALYTIC 1,6-ADDITION C-H Functionalization DIVERGENT SYNTHESIS PARA-QUINONE METHIDES Regioselectity SOLVENT |
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| Snippet | Grignard reagent‐mediated and solvent‐controlled regioselective 1,8‐addition of α‐(2‐thienylidene)‐β‐ketosulfones provides diversified substituted... Grignard reagent-mediated and solventcontrolled regioselective 1,8-addition of alpha-(2-thienylidene)-beta-ketosulfones provides diversified substituted... |
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| SubjectTerms | Addition Bromides Chemistry Chemistry, Applied Chemistry, Organic Cosolvent C−H Functionalization Diethyl ether Physical Sciences Reagents Regioselectity Regioselectivity Science & Technology Solvents Transition metals β-Ketosulfone |
| Title | Grignard Reagent‐Mediated Regioselective 1,8‐Addition of α‐(2‐Thienylidene)‐β‐ketosulfones |
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