Mechanistic insight for tunable regioselective cyclization of aryl propiolates with radicals:<i>ipso</i>-<i>versus ortho</i>-cyclization

Fıstıkçı, Meryem

doi:10.1039/d3nj02030d

New J. Chem.

2023

DOI: 10.1039/d3nj02030d

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Mechanistic insight for tunable regioselective cyclization of aryl propiolates with radicals:ipso-versus ortho-cyclization

Meryem Fıstıkçı

Abstract: A computational study of the reaction mechanism of aryl propiolates with various radicals is examined employing DFT and coupled-cluster methods at the DLPNO-CCSD(T)/cc-pVTZ//M062X-6-311G(d,p) level. Computations demonstrated that the reaction mechanism...

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2024

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Photoredox/Iron Dual-Catalysis-Enabled [4 + 2] Cyclization of Acyl Nitrene with Alkynes

Xie,

Tang,

Hou

et al. 2024

Org. Lett.

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In this work, the annulation of acyl nitrene with alkynes is reported under photoredox/iron dual-catalysis for the synthesis of a series of isoquninalin-2-ones. The reaction is featured with a high reaction regioselectivity and good reaction generality. In particular, the resulting isoquinalin-2-ones could be structurally elaborated into several biologically interesting scaffolds. Mechanism investigation suggests that the reaction was ascribed to a formal [4 + 2] cyclization. It is believed that this reaction represents an initial example of preparing isoquinolin-1-ones from ferric peroxylcatalyzed nitrene insertion.

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Photoredox/Iron Dual-Catalysis-Enabled [4 + 2] Cyclization of Acyl Nitrene with Alkynes

Xie,

Tang,

Hou

et al. 2024

Org. Lett.

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Theoretical investigation of a chiral Brønsted acid (CBA)-catalyzed isomerization reaction of BCB: mechanism and origin of stereoselectivity

Wang,

Wang

2024

New J. Chem.

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Mechanistic insight for tunable regioselective cyclization of aryl propiolates with radicals:ipso-versus ortho-cyclization

Abstract: A computational study of the reaction mechanism of aryl propiolates with various radicals is examined employing DFT and coupled-cluster methods at the DLPNO-CCSD(T)/cc-pVTZ//M062X-6-311G(d,p) level. Computations demonstrated that the reaction mechanism...

Cited by 2 publications

References 53 publications

Photoredox/Iron Dual-Catalysis-Enabled [4 + 2] Cyclization of Acyl Nitrene with Alkynes

Photoredox/Iron Dual-Catalysis-Enabled [4 + 2] Cyclization of Acyl Nitrene with Alkynes

Theoretical investigation of a chiral Brønsted acid (CBA)-catalyzed isomerization reaction of BCB: mechanism and origin of stereoselectivity

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