Regioselective Conversion of Arenes to <i>N</i>‐aryl‐1,2,3‐triazoles Using CH Borylation

Srinivasan, Rajavel; Coyne, Anthony G.; Abell, Chris

doi:10.1002/chem.201403021

Cited by 19 publications

(2 citation statements)

References 64 publications

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“…Since azide is one of the prototypical triazole precursors, in-situ azide generation will simplify triazole introduction. Abell and Sirinivasan successfully converted arenes to N -aryl-1,2,3-triazoles through a one-pot tandem reaction, which was initiated from C–H bond borylation, followed by copper-catalyzed azidation and azide–alkyne click reaction at the end 358 . This approach was applied to equip (±)- α -tocopherol nicotinate, nicotine, and resveratrol with triazole ( Scheme 30 a).…”

Section: Nitrogenation Of Bioactive Compoundsmentioning

confidence: 99%

Late-stage modification of bioactive compounds: Improving druggability through efficient molecular editing

Huo,

Zhao,

Cheng

et al. 2024

Acta Pharmaceutica Sinica B

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Section: Nitrogenation Of Bioactive Compoundsmentioning

confidence: 99%

Late-stage modification of bioactive compounds: Improving druggability through efficient molecular editing

Huo,

Zhao,

Cheng

et al. 2024

Acta Pharmaceutica Sinica B

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“…The telescoped borylation−azidation sequence was applied to the synthesis of triazole-substituted arenes, including a resveratrol analogue and a nicotine derivative (Scheme 61). 120 In 2019, Srinivasan et al developed copper-mediated conditions for the nitration of aryl boronic esters. This reaction, in combination with C−H borylation, enables the rapid synthesis of nitroarenes and the corresponding anilines.…”

Section: Transition-metal-catalyzed Borylation Of C−h Bonds In the Sy...mentioning

confidence: 99%

Transition-Metal-Catalyzed Silylation and Borylation of C–H Bonds for the Synthesis and Functionalization of Complex Molecules

Yu,

Wilson,

Hartwig

2023

Chem. Rev.

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The functionalization of C−H bonds in organic molecules containing functional groups has been one of the holy grails of catalysis. One synthetically important approach to the diverse functionalization of C−H bonds is the catalytic silylation or borylation of C−H bonds, which enables a broad array of downstream transformations to afford diverse structures. Advances in both undirected and directed methods for the transition-metal-catalyzed silylation and borylation of C−H bonds have led to their rapid adoption in early-, mid-, and late-stage of the synthesis of complex molecules. In this Review, we review the application of the transition-metal-catalyzed silylation and borylation of C−H bonds to the synthesis of bioactive molecules, organic materials, and ligands. Overall, we aim to provide a picture of the state of art of the silylation and borylation of C−H bonds as applied to the synthesis and modification of diverse architectures that will spur further application and development of these reactions.

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Combining Copper‐Catalyzed Hydroboration with Palladium‐Catalyzed Suzuki Coupling for the One‐pot Synthesis of Arylallylamines under Micellar Conditions

et al. 2017

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Herein we report the one‐pot dual‐metal catalytic synthesis of arylallylamines, by combination of a Cu‐catalyzed hydroboration with a Pd‐catalyzed Suzuki arylation, using a broad range of aryl halides. Importantly, the reaction sequence was entirely performed in water, in the presence of small amounts of SPGS‐550M, without the need of solvent switch or addition of organic co‐solvents, rendering it operationally simple and environmentally benign. The usefulness of this methodology was highlighted in a short synthesis of the pharmaceutically important compound naftifine.magnified image

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Regioselective Conversion of Arenes to N‐aryl‐1,2,3‐triazoles Using CH Borylation

Cited by 19 publications

References 64 publications

Late-stage modification of bioactive compounds: Improving druggability through efficient molecular editing

Late-stage modification of bioactive compounds: Improving druggability through efficient molecular editing

Transition-Metal-Catalyzed Silylation and Borylation of C–H Bonds for the Synthesis and Functionalization of Complex Molecules

Combining Copper‐Catalyzed Hydroboration with Palladium‐Catalyzed Suzuki Coupling for the One‐pot Synthesis of Arylallylamines under Micellar Conditions

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