Uncanonical Semireduction of Quinolines and Isoquinolines via Regioselective HAT-Promoted Hydrosilylation

Heterocycles are the backbone of modern medical chemistry and drug development. The derivatization of “an olefin” inside aromatic rings represents an ideal approach to access functionalized saturated heterocycles from abundant aromatic building blocks. Here, we report an operationally simple, effici...

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Published inJournal of the American Chemical Society Vol. 145; no. 1; pp. 25 - 31
Main Authors Hu, Chao, Vo, Cuong, Merchant, Rohan R., Chen, Si-Jie, Hughes, Jonathan M. E., Peters, Byron K., Qin, Tian
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 11.01.2023
Subjects
Catalysis
Drug Development
Isoquinolines
Molecular Structure
Quinolines
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Summary:Heterocycles are the backbone of modern medical chemistry and drug development. The derivatization of “an olefin” inside aromatic rings represents an ideal approach to access functionalized saturated heterocycles from abundant aromatic building blocks. Here, we report an operationally simple, efficient, and practical method to selectively access hydrosilylated and reduced N-heterocycles from bicyclic aromatics via a key diradical intermediate. This approach is expected to facilitate complex heterocycle functionalizations that enable access to novel medicinally relevant scaffolds.
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content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.2c11664