Silylation of 2<i>H</i>-indazoles by photoinduced hydrogen atom transfer catalysis

Das, Krishna Kanta; Hajra, Alakananda

doi:10.1039/d3ob01925j

Org. Biomol. Chem.

2024

DOI: 10.1039/d3ob01925j

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Silylation of 2H-indazoles by photoinduced hydrogen atom transfer catalysis

Krishna Kanta Das,

Alakananda Hajra

Abstract: A metal-free visible-light-mediated C−H silylation of 2H-indazoles with triphenylsilane has been developed employing 4CzIPN as a photocatalyst and triisopropylsilanethiol as a hydrogen atom transfer (HAT) reagent under aerobic reaction conditions....

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Cited by 6 publications

References 64 publications

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Visible‐Light‐Induced C−H Silylation of Azauracils with Hydrosilanes

Yu,

You,

et al. 2024

Adv Synth Catal

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A C–H silylation of azauracils was developed via the combination of organic photoredox and hydrogen atom transfer (HAT) catalysis. Using 1,2,3,5‐tetrakis(carbazol‐9‐yl)‐4,6‐dicyanobenzene (4CzIPN) as the photocatalyst, quinuclidine as the HAT catalyst, and silanes as the silyl radical sources, a variety of silylated azauracils were synthesized in 43‐87% yields. Moreover, pyrazinone, cinnolinone, and chromone were also compatible with this catalytic system. The reaction is suitable for late‐stage functionalization of drugs and complex molecules, and the transformation can be easily scaled up to the gram level. Mechanistic studies suggest that the silylation reaction is likely to proceed through a radical mechanism.

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Visible‐Light‐Induced C−H Silylation of Azauracils with Hydrosilanes

Yu,

You,

et al. 2024

Adv Synth Catal

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Cu(I)‐Catalyzed Silylation and Germylation of Azauracils

Mahato,

Ghosh,

Hajra

2024

Chemistry A European J

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The current study demonstrates a Cu(I) catalyzed direct C(sp2)‐H silylation and germylation of azauracil using triphenylsilane and triphenylgermane. A broad scope, excellent functional group tolerance, and suitability for large‐scale reactions are exhibited in this protocol. Moreover, this method can be readily applied to structurally complex bioactive molecules. Experimental results suggest a radical mechanistic pathway for the reaction.

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Organophotocatalytic Regioselective Silylation/Germylation and Cascade Cyclization of N-Alkenyl α-CF₃ Acrylamides: Access to Densely Functionalized 4-Pyrrolin-2-ones

Bajya,

Maurya,

Selvakumar

2024

Org. Lett.

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We report an organophotoredox-catalyzed silylation/germylation cascade cyclization of N-alkenyl α-CF 3 acrylamides under mild conditions. N-Aminopyridinium salts act as hydrogen atom transfer reagents under photoredox catalysis in the generation of silyl and germyl radicals. An array of silyl-and germyl-substituted 3-CF 3 -4-pyrrolin-2-one derivatives were constructed in a shorter reaction time with low catalyst loading in good to excellent yields at room temperature. Importantly, this protocol is amenable to the late-stage diversification of bioactive molecules, as well as to large-scale synthesis.

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Silylation of 2H-indazoles by photoinduced hydrogen atom transfer catalysis

Abstract: A metal-free visible-light-mediated C−H silylation of 2H-indazoles with triphenylsilane has been developed employing 4CzIPN as a photocatalyst and triisopropylsilanethiol as a hydrogen atom transfer (HAT) reagent under aerobic reaction conditions....

Cited by 6 publications

References 64 publications

Visible‐Light‐Induced C−H Silylation of Azauracils with Hydrosilanes

Visible‐Light‐Induced C−H Silylation of Azauracils with Hydrosilanes

Cu(I)‐Catalyzed Silylation and Germylation of Azauracils

Organophotocatalytic Regioselective Silylation/Germylation and Cascade Cyclization of N-Alkenyl α-CF₃ Acrylamides: Access to Densely Functionalized 4-Pyrrolin-2-ones

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Silylation of 2H-indazoles by photoinduced hydrogen atom transfer catalysis

Abstract: A metal-free visible-light-mediated C−H silylation of 2H-indazoles with triphenylsilane has been developed employing 4CzIPN as a photocatalyst and triisopropylsilanethiol as a hydrogen atom transfer (HAT) reagent under aerobic reaction conditions....

Cited by 6 publications

References 64 publications

Visible‐Light‐Induced C−H Silylation of Azauracils with Hydrosilanes

Visible‐Light‐Induced C−H Silylation of Azauracils with Hydrosilanes

Cu(I)‐Catalyzed Silylation and Germylation of Azauracils

Organophotocatalytic Regioselective Silylation/Germylation and Cascade Cyclization of N-Alkenyl α-CF3 Acrylamides: Access to Densely Functionalized 4-Pyrrolin-2-ones

Contact Info

Product

Resources

About

Organophotocatalytic Regioselective Silylation/Germylation and Cascade Cyclization of N-Alkenyl α-CF₃ Acrylamides: Access to Densely Functionalized 4-Pyrrolin-2-ones