Electrochemical C(sp<sup>3</sup>)–C(sp<sup>3</sup>) cross-dehydrogenative coupling: enabling access to 9-substituted fluorescent acridanes

Roy, Shantonu; Karmakar, Sudip; Mondal, Imtiaj; Naskar, Koushik; Sarkar, Writhabrata; Deb, Indubhusan

doi:10.1039/d3cc02127k

Chem. Commun.

2023

DOI: 10.1039/d3cc02127k

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Electrochemical C(sp³)–C(sp³) cross-dehydrogenative coupling: enabling access to 9-substituted fluorescent acridanes

Shantonu Roy

Sudip Karmakar

Imtiaj Mondal

et al.

Abstract: A straightforward strategy for direct access of C-9 functionalized N-alkyl-acridanes in good to excellent yields has been established via metal and external oxidant-free sustainable electrochemical C(sp3)-C(sp3) cross-dehydrogenative coupling reaction between...

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Cited by 4 publications

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Organocatalyzed Electrochemical Enantioselective α‐Alkylation of Aldehydes with 9,10‐Dihydroacridines

He,

Wang,

Zhao

et al. 2024

Eur J Org Chem

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Acridine scaffolds are present in biological and pharmaceutical molecules. However, achieving asymmetric functionalization of acridines remains challenging without an efficient and highly stereoselective approach. Here we demonstrate a facile electrooxidative asymmetric dehydrogenative coupling reaction of 9,10‐dihydroacridines with aldehydes. This method offers a sustainable and effective route to various chiral α‐alkylation of 9,10‐dihydroacridines in high yields with excellent enantioselectivities facilitated by readily available aminocatalyst. Detailed mechanistic studies and cyclic voltammetric analyses reveal that this asymmetric electrochemical reaction proceeds through redox‐mediated oxidation, followed by a nucleophilic attack with concurrently generated enamine. We anticipate that our research will open avenues for promising exploration in organocatalyzed electrochemical enantioselective transformations.

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Organocatalyzed Electrochemical Enantioselective α‐Alkylation of Aldehydes with 9,10‐Dihydroacridines

He,

Wang,

Zhao

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

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Electrochemical Promoted Three-Component Trifluoromethylation/Spirocyclization Reaction of N-Arylsulfonylacrylamides to 4-Azaspiro[4.5]decanes

Lei,

Liu,

Cui

et al. 2023

Org. Lett.

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An electrochemical facilitated three-component trifluoromethylation/spirocyclization reaction of N-(arylsulfonyl)acrylamides, CF3SO2Na, and H2O has been developed. Without the requirement of chemical oxidants, a number of unexplored trifluoromethylated 4-azaspiro[4.5]decanes were obtained in satisfactory yields under mild conditions. This work provides a new synthetic strategy for fluorine-containing spirocyclic compounds and shows a new perspective for the reactivity study of N-(arylsulfonyl)acrylamides.

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Direct alkylation of quinoxalinones with electron-deficient alkenes enabled by a sequential paired electrolysis

Wang,

Liu,

Sun

et al. 2023

Chem. Commun.

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Electrochemical C(sp³)–C(sp³) cross-dehydrogenative coupling: enabling access to 9-substituted fluorescent acridanes

Abstract: A straightforward strategy for direct access of C-9 functionalized N-alkyl-acridanes in good to excellent yields has been established via metal and external oxidant-free sustainable electrochemical C(sp3)-C(sp3) cross-dehydrogenative coupling reaction between...

Cited by 4 publications

References 27 publications

Organocatalyzed Electrochemical Enantioselective α‐Alkylation of Aldehydes with 9,10‐Dihydroacridines

Organocatalyzed Electrochemical Enantioselective α‐Alkylation of Aldehydes with 9,10‐Dihydroacridines

Electrochemical Promoted Three-Component Trifluoromethylation/Spirocyclization Reaction of N-Arylsulfonylacrylamides to 4-Azaspiro[4.5]decanes

Direct alkylation of quinoxalinones with electron-deficient alkenes enabled by a sequential paired electrolysis

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Electrochemical C(sp3)–C(sp3) cross-dehydrogenative coupling: enabling access to 9-substituted fluorescent acridanes

Abstract: A straightforward strategy for direct access of C-9 functionalized N-alkyl-acridanes in good to excellent yields has been established via metal and external oxidant-free sustainable electrochemical C(sp3)-C(sp3) cross-dehydrogenative coupling reaction between...

Cited by 4 publications

References 27 publications

Organocatalyzed Electrochemical Enantioselective α‐Alkylation of Aldehydes with 9,10‐Dihydroacridines

Organocatalyzed Electrochemical Enantioselective α‐Alkylation of Aldehydes with 9,10‐Dihydroacridines

Electrochemical Promoted Three-Component Trifluoromethylation/Spirocyclization Reaction of N-Arylsulfonylacrylamides to 4-Azaspiro[4.5]decanes

Direct alkylation of quinoxalinones with electron-deficient alkenes enabled by a sequential paired electrolysis

Contact Info

Product

Resources

About

Electrochemical C(sp³)–C(sp³) cross-dehydrogenative coupling: enabling access to 9-substituted fluorescent acridanes