Decarboxylative\nAminomethylation of Indole-3-carboxylic\nAcids via Strain Release-Driven Ring Opening of 1,2-Oxazetidines

A copper-catalyzed decarboxylative aminomethylation of\nindole-3-carboxylic\nacids with 1,2-oxazetidines has been developed, enabling the rapid\nsynthesis of structurally diverse 3-aminomethylindoles in good to\nexcellent yields. Remarkably, an unprecedented decarboxylative aminomethylation/cyclization\ncascade was further achieved by a combination of copper and iron salts\nto construct complex γ-carbolines with high efficiency. It is\nworth noting that one of the obtained products proved to be a good\ndual-emissive luminogen, exhibiting both aggregation-caused quenching\nand aggregation-induced emission.

Publication Details

Journal
Figshare
Published
2024-10-09
DOI
https://doi.org/10.1021/acs.orglett.4c03426.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Decarboxylative\nAminomethylation of Indole-3-carboxylic\nAcids via Strain Release-Driven Ring Opening of 1,2-Oxazetidines

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Catalytic C–H Functionalization Methods
article

Decarboxylative\nAminomethylation of Indole-3-carboxylic\nAcids via Strain Release-Driven Ring Opening of 1,2-Oxazetidines

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Abstract

A copper-catalyzed decarboxylative aminomethylation of\nindole-3-carboxylic\nacids with 1,2-oxazetidines has been developed, enabling the rapid\nsynthesis of structurally diverse 3-aminomethylindoles in good to\nexcellent yields. Remarkably, an unprecedented decarboxylative aminomethylation/cyclization\ncascade was further achieved by a combination of copper and iron salts\nto construct complex γ-carbolines with high efficiency. It is\nworth noting that one of the obtained products proved to be a good\ndual-emissive luminogen, exhibiting both aggregation-caused quenching\nand aggregation-induced emission.

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Catalytic C–H Functionalization Methods
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Decarboxylative\nAminomethylation of Indole-3-carboxylic\nAcids via Strain Release-Driven Ring Opening of 1,2-Oxazetidines · Figshare (2024) | TGRS Research Map | TGRS