C(sp3)–C(sp3) Coupling of Cycloalkanes and Alkyl Halides via Dual Photocatalytic Hydrogen Atom Transfer and Nickel Catalysis

Functionalization of C­(sp3)–H bonds represents the most straightforward and atom-economical transformation in organic synthesis. An innovative approach integrating photocatalytic hydrogen atom transfer (HAT) and transition metal catalysis has made significant progress in the coupling of α-heterosub...

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Published inOrganic letters Vol. 26; no. 15; pp. 2993 - 2998
Main Authors Pilli, Ramadevi, Selvam, Keerthika, Balamurugan, Bala S. S., Jose, Vidya, Rasappan, Ramesh
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.04.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACTIVATION
NATURAL-PRODUCTS
ESTERS
BONDS
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Summary:Functionalization of C­(sp3)–H bonds represents the most straightforward and atom-economical transformation in organic synthesis. An innovative approach integrating photocatalytic hydrogen atom transfer (HAT) and transition metal catalysis has made significant progress in the coupling of α-heterosubstituted C–H bonds with alkyl halides. However, unactivated alkanes were ineffective as a result of the preponderance of byproduct formation. Herein, we demonstrate direct HAT and nickel catalysis in the coupling of cycloalkanes and benzyl bromides/primary alkyl iodides. Additionally, tetrabutylammonium decatungstate (TBADT) was recovered and recycled.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c00567