Photoinduced Multicomponent Heteroarylation of [1.1.1]Propellane\nwith Katritzky Pyridinium Salts

(Hetero)arylated\nbicyclo[1.1.1]pentanes (BCPs) are important for\nthe construction of complex druglike target molecules. Herein, we\ndeveloped a method for light-induced, Cs<sub>2</sub>CO<sub>3</sub>-promoted homolytic cleavage of pyridinium C–N bonds for generating\nalkyl radicals from amino acid-derived Katritzky salts and use of\nthe radicals for functionalization of [1.1.1]propellane to rapidly\ngenerate (hetero)arylated BCPs. The method features excellent functional\ngroup tolerance and a broad substrate scope and can be used to functionalize\nstructurally complex natural products.

Publication Details

Journal
Figshare
Published
2024-08-14
DOI
https://doi.org/10.1021/acs.orglett.4c02571.s001
Primary Topic
Wheat and Barley Genetics and Pathology
Type
article
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article

Photoinduced Multicomponent Heteroarylation of [1.1.1]Propellane\nwith Katritzky Pyridinium Salts

Figshare
Wheat and Barley Genetics and Pathology
article

Photoinduced Multicomponent Heteroarylation of [1.1.1]Propellane\nwith Katritzky Pyridinium Salts

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Abstract

(Hetero)arylated\nbicyclo[1.1.1]pentanes (BCPs) are important for\nthe construction of complex druglike target molecules. Herein, we\ndeveloped a method for light-induced, Cs<sub>2</sub>CO<sub>3</sub>-promoted homolytic cleavage of pyridinium C–N bonds for generating\nalkyl radicals from amino acid-derived Katritzky salts and use of\nthe radicals for functionalization of [1.1.1]propellane to rapidly\ngenerate (hetero)arylated BCPs. The method features excellent functional\ngroup tolerance and a broad substrate scope and can be used to functionalize\nstructurally complex natural products.

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Openalex Percentile: Top 41%
Wheat and Barley Genetics and Pathology
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Photoinduced Multicomponent Heteroarylation of [1.1.1]Propellane\nwith Katritzky Pyridinium Salts · Figshare (2024) | TGRS Research Map | TGRS