A visible-light-induced photosensitizer-free decarbonylative Minisci-type reaction

Qi, Ming; Xu, An-Wu

doi:10.1039/d4ob00021h

Org. Biomol. Chem.

2024

DOI: 10.1039/d4ob00021h

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A visible-light-induced photosensitizer-free decarbonylative Minisci-type reaction

Ming Qi,

An-Wu Xu

Abstract: This study presents a green and practical visible-light-induced photosensitizer-free decarbonylative Minisci-type reaction using aldehydes as alkyl radical precursors. Mechanism experiments revealed that TFA could absorb light and activate N-heteroarenes, promoting...

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Photocatalyst‐Free Chiral Phosphoric Acid‐Catalyzed Enantioselective Minisci‐Type Alkylation of N‐Heteroarenes

Jin,

Li,

Wang

et al. 2024

Eur J Org Chem

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In this study, we present an efficient radical approach for the enantioselective Minisci‐type alkylation of N‐heteroarenes, using chiral phosphoric acid (CPA) as a catalyst under mild conditions, without the need for metals, photocatalysts, and other additives. Prochiral α‐aminoalkyl radicals generated from RAEs were successfully introduced to N‐heteroarene derivatives, including pyridine, quinoline, and isoquinoline, resulting in a range of valuable chiral alkylated N‐heteroarenes with secondary amines in high yields and good to excellent enantioselectivities (up to 98% ee). The chiral phosphoric acid catalyst not only activates the substrate and induces asymmetry but also facilitates essential electron transfer processes.

show abstract

Photocatalyst‐Free Chiral Phosphoric Acid‐Catalyzed Enantioselective Minisci‐Type Alkylation of N‐Heteroarenes

Jin,

Li,

Wang

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

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A visible-light-induced photosensitizer-free decarbonylative Minisci-type reaction

Abstract: This study presents a green and practical visible-light-induced photosensitizer-free decarbonylative Minisci-type reaction using aldehydes as alkyl radical precursors. Mechanism experiments revealed that TFA could absorb light and activate N-heteroarenes, promoting...

Cited by 1 publication

References 65 publications

Photocatalyst‐Free Chiral Phosphoric Acid‐Catalyzed Enantioselective Minisci‐Type Alkylation of N‐Heteroarenes

Photocatalyst‐Free Chiral Phosphoric Acid‐Catalyzed Enantioselective Minisci‐Type Alkylation of N‐Heteroarenes

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