Cobalt‐Promoted <i>Para</i> C─H Amination of 3‐Acetyl Substituted Nitroarenes with Arylhydrazines

Abstract We report a method to furnish substituted 1H ‐indazoles via a coupling of 3‐acetyl substituted nitroarenes and arylhydrazines. Reactions progressed in the presence of cobalt(II) acetylacetonate catalyst, TEMPO oxidant, and Cs 2 CO 3 base. Functional groups including bromo, chloro, nitro, and trifluoromethoxy groups were compatible with reaction conditions. The proposed mechanism was based on a nucleophilic substitution of hydrogen para to nitro group. Our method feature a convenient pathway to directly obtain substituted 1H ‐indazoles which avoid the use of pre‐functionalized starting materials. Indazole could play a role as the directing group for a palladium‐catalyzed C(sp 2 )─H arylation with iodobenzene.

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Publication Details

Journal
ChemistrySelect
Published
2024-11-01
DOI
https://doi.org/10.1002/slct.202402834
Citations
1
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.25

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article

Cobalt‐Promoted Para C─H Amination of 3‐Acetyl Substituted Nitroarenes with Arylhydrazines

Tung Thanh Nguyen, Duyen K. Nguyen, Giang Binh Tran
1 citations
ChemistrySelect
Catalytic C–H Functionalization Methods
0.25
article

Cobalt‐Promoted Para C─H Amination of 3‐Acetyl Substituted Nitroarenes with Arylhydrazines

Tung Thanh Nguyen, Duyen K. Nguyen, Giang Binh Tran
article en
1 citations

Abstract

Abstract We report a method to furnish substituted 1H ‐indazoles via a coupling of 3‐acetyl substituted nitroarenes and arylhydrazines. Reactions progressed in the presence of cobalt(II) acetylacetonate catalyst, TEMPO oxidant, and Cs 2 CO 3 base. Functional groups including bromo, chloro, nitro, and trifluoromethoxy groups were compatible with reaction conditions. The proposed mechanism was based on a nucleophilic substitution of hydrogen para to nitro group. Our method feature a convenient pathway to directly obtain substituted 1H ‐indazoles which avoid the use of pre‐functionalized starting materials. Indazole could play a role as the directing group for a palladium‐catalyzed C(sp 2 )─H arylation with iodobenzene.

ChemistrySelectVol. 9(43)
Vietnam National University Ho Chi Minh City (VN), Ho Chi Minh City University of Technology (VN)
Viet Nam National University Ho Chi Minh City
Clean water and sanitation
Openalex Percentile: Top 46%
Catalytic C–H Functionalization Methods
0.25
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Cobalt‐Promoted <i>Para</i> C─H Amination of 3‐Acetyl Substituted Nitroarenes with Arylhydrazines — Tung Thanh Nguyen, Duyen K. Nguyen, et al. · ChemistrySelect (2024) | TGRS Research Map | TGRS