Silyl Radical Mediated Cross-Electrophile Coupling of N‑Acyl-imides with Alkyl Bromides under Photoredox/Nickel Dual Catalysis

Silyl Radical Mediated Cross-Electrophile Coupling of N‑Acyl-imides with Alkyl Bromides under Photoredox/Nickel Dual Catalysis

A photoredox Ni-catalyzed cross-coupling of N-acyl-imides with unactivated alkyl bromides has been developed that enables efficient access to a variety of functionalized alkyl ketones, including unsymmetrical dialkyl ketones, under very mild and operationally practical conditions. The reaction that...

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Veröffentlicht in:Organic letters 2020-03, Vol.22 (6), p.2240-2245
Hauptverfasser: Kerackian, Taline, Reina, Antonio, Bouyssi, Didier, Monteiro, Nuno, Amgoune, Abderrahmane
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Organic chemistry
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container_end_page 2245
container_issue 6
container_start_page 2240
container_title Organic letters
container_volume 22
creator Kerackian, Taline
Reina, Antonio
Bouyssi, Didier
Monteiro, Nuno
Amgoune, Abderrahmane
description A photoredox Ni-catalyzed cross-coupling of N-acyl-imides with unactivated alkyl bromides has been developed that enables efficient access to a variety of functionalized alkyl ketones, including unsymmetrical dialkyl ketones, under very mild and operationally practical conditions. The reaction that operates without the need for any preformed carbon nucleophile proceeds via the combination of two different bond activation processes, i.e. Ni-catalyzed imide activation via C­(acyl)–N bond cleavage and (TMS)3Si radical-mediated alkyl halide activation via halogen-atom abstraction.
doi_str_mv 10.1021/acs.orglett.0c00442
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title Silyl Radical Mediated Cross-Electrophile Coupling of N‑Acyl-imides with Alkyl Bromides under Photoredox/Nickel Dual Catalysis
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