Acridine photocatalysis enables tricomponent direct decarboxylative amine construction

Sui, Xianwei; Dang, Hang T.; Porey, Arka; Trevino, Ramon; Das, Arko; Fremin, Seth O.; Hughes, William B.; Thompson, William T.; Dhakal, Shree Krishna; Arman, Hadi D.; Larionov, Oleg V.

doi:10.1039/d4sc02356k

Chem. Sci.

2024

DOI: 10.1039/d4sc02356k

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Acridine photocatalysis enables tricomponent direct decarboxylative amine construction

Xianwei Sui,

Hang T. Dang,

Arka Porey

et al.

Abstract: Amines are centrally important motifs in medicinal chemistry and biochemistry, and indispensable intermediates and linchpins in organic synthesis. Despite their cross-disciplinary prominence, synthetic access to amine continues to rely on...

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Cited by 3 publications

References 80 publications

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Visible-Light-Driven Synthesis of N-Alkyl α-Amino Acid Derivatives from Unactivated Alkyl Bromides and In Situ Generated Imines

Yang,

Qiu,

et al. 2024

Org. Lett.

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Visible-Light-Driven Synthesis of N-Alkyl α-Amino Acid Derivatives from Unactivated Alkyl Bromides and In Situ Generated Imines

Yang,

Qiu,

et al. 2024

Org. Lett.

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Acridine/Lewis Acid Complexes as Powerful Photocatalysts: A Combined Experimental and Mechanistic Study

Rickertsen,

Crow,

Das

et al. 2024

ACS Catal.

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Photocatalytic Decarboxylative Alkylation of Cyclic Imine–BF₃ Complexes: A Modular Route to Functionalized Azacycles

Bhatt,

Adili,

Tran

et al. 2024

J. Am. Chem. Soc.

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Alkyl radicals generated via an acridine photocatalyzed decarboxylation reaction of feedstock carboxylic acids engage with a range of cyclic imine–BF3 complexes to provide α-functionalized azacycles in an operationally simple process. A three-component variant of this transformation incorporating [1.1.1]propellane as an additional reaction partner enables the synthesis of valuable bicyclopentane (BCP)-containing azacycles. Reactions exhibit good functional group compatibility, enabling late-stage modification of complex bioactive molecules.

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Acridine photocatalysis enables tricomponent direct decarboxylative amine construction

Abstract: Amines are centrally important motifs in medicinal chemistry and biochemistry, and indispensable intermediates and linchpins in organic synthesis. Despite their cross-disciplinary prominence, synthetic access to amine continues to rely on...

Cited by 3 publications

References 80 publications

Visible-Light-Driven Synthesis of N-Alkyl α-Amino Acid Derivatives from Unactivated Alkyl Bromides and In Situ Generated Imines

Visible-Light-Driven Synthesis of N-Alkyl α-Amino Acid Derivatives from Unactivated Alkyl Bromides and In Situ Generated Imines

Acridine/Lewis Acid Complexes as Powerful Photocatalysts: A Combined Experimental and Mechanistic Study

Photocatalytic Decarboxylative Alkylation of Cyclic Imine–BF₃ Complexes: A Modular Route to Functionalized Azacycles

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Acridine photocatalysis enables tricomponent direct decarboxylative amine construction

Abstract: Amines are centrally important motifs in medicinal chemistry and biochemistry, and indispensable intermediates and linchpins in organic synthesis. Despite their cross-disciplinary prominence, synthetic access to amine continues to rely on...

Cited by 3 publications

References 80 publications

Visible-Light-Driven Synthesis of N-Alkyl α-Amino Acid Derivatives from Unactivated Alkyl Bromides and In Situ Generated Imines

Visible-Light-Driven Synthesis of N-Alkyl α-Amino Acid Derivatives from Unactivated Alkyl Bromides and In Situ Generated Imines

Acridine/Lewis Acid Complexes as Powerful Photocatalysts: A Combined Experimental and Mechanistic Study

Photocatalytic Decarboxylative Alkylation of Cyclic Imine–BF3 Complexes: A Modular Route to Functionalized Azacycles

Contact Info

Product

Resources

About

Photocatalytic Decarboxylative Alkylation of Cyclic Imine–BF₃ Complexes: A Modular Route to Functionalized Azacycles