Photoredox cross-dehydrogenative C(sp<sup>2</sup>)–C(sp<sup>3</sup>) coupling of heteroarenes with secondary amines through 1,5-HAT

Srinivasu, Vinjamuri; Pattanaik, Swadhin; Sureshkumar, Devarajulu

doi:10.1039/d4cc02818j

Chem. Commun.

2024

DOI: 10.1039/d4cc02818j

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Photoredox cross-dehydrogenative C(sp²)–C(sp³) coupling of heteroarenes with secondary amines through 1,5-HAT

Vinjamuri Srinivasu,

Swadhin Pattanaik,

Devarajulu Sureshkumar

Abstract: The functionalization of α-C(sp3)–H bonds in amines has become a focal point of contemporary research. Here, we report a new approach utilizing photocatalysis a-C(sp3)-H bond functionalization in alicyclic and aliphatic...

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Electron Donor–Acceptor Complex-Driven Divergent Routes to α-Amino Bicyclopentyl Iodides and Methylene Cyclobutanols

Srinivasu,

Pal,

Giri

et al. 2024

Org. Lett.

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Amines are essential due to their structural diversity and biological significance. Introducing the valuable bicyclopentane (BCP) moiety at the α-position of amines offers a promising strategy for developing novel bioactive compounds. This study outlines a divergent synthesis approach to generate α-aminofunctionalized bicyclopentyl iodides and methylene cyclobutanols under mild and environmentally sustainable conditions. By employing an electron donor−acceptor (EDA) complex between amine and the inexpensive and readily available inorganic base Cs 2 CO 3 , this method circumvents the need for strongly reducing, metal-based photocatalysts typically required for aryl radical generation. This approach enables the α-functionalization of various aliphatic and alicyclic amines via a 1,5-hydrogen atom transfer mechanism.

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Electron Donor–Acceptor Complex-Driven Divergent Routes to α-Amino Bicyclopentyl Iodides and Methylene Cyclobutanols

Srinivasu,

Pal,

Giri

et al. 2024

Org. Lett.

View full text Add to dashboard Cite

show abstract

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Photoredox cross-dehydrogenative C(sp²)–C(sp³) coupling of heteroarenes with secondary amines through 1,5-HAT

Abstract: The functionalization of α-C(sp3)–H bonds in amines has become a focal point of contemporary research. Here, we report a new approach utilizing photocatalysis a-C(sp3)-H bond functionalization in alicyclic and aliphatic...

Cited by 1 publication

References 32 publications

Electron Donor–Acceptor Complex-Driven Divergent Routes to α-Amino Bicyclopentyl Iodides and Methylene Cyclobutanols

Electron Donor–Acceptor Complex-Driven Divergent Routes to α-Amino Bicyclopentyl Iodides and Methylene Cyclobutanols

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Photoredox cross-dehydrogenative C(sp2)–C(sp3) coupling of heteroarenes with secondary amines through 1,5-HAT

Abstract: The functionalization of α-C(sp3)–H bonds in amines has become a focal point of contemporary research. Here, we report a new approach utilizing photocatalysis a-C(sp3)-H bond functionalization in alicyclic and aliphatic...

Cited by 1 publication

References 32 publications

Electron Donor–Acceptor Complex-Driven Divergent Routes to α-Amino Bicyclopentyl Iodides and Methylene Cyclobutanols

Electron Donor–Acceptor Complex-Driven Divergent Routes to α-Amino Bicyclopentyl Iodides and Methylene Cyclobutanols

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Product

Resources

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Photoredox cross-dehydrogenative C(sp²)–C(sp³) coupling of heteroarenes with secondary amines through 1,5-HAT