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. 2019 Jun 27;10(33):7728-7733.
doi: 10.1039/c9sc02616a. eCollection 2019 Sep 7.

A dual photoredox-nickel strategy for remote functionalization via iminyl radicals: radical ring-opening-arylation, -vinylation and -alkylation cascades

Elizabeth M Dauncey  1 , Shashikant U Dighe  1 , James J Douglas  2 , Daniele Leonori  1
Affiliations

A dual photoredox-nickel strategy for remote functionalization via iminyl radicals: radical ring-opening-arylation, -vinylation and -alkylation cascades

Elizabeth M Dauncey et al. Chem Sci. .

Erratum in

Abstract

A divergent strategy for the remote arylation, vinylation and alkylation of nitriles is described. These processes proceed through the photoredox generation of a cyclic iminyl radical and its following ring-opening reaction. The distal nitrile radical is then engaged in nickel-based catalytic cycles to form C-C bonds with aryl bromides, alkynes and alkyl bromides.

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Figures

Scheme 1
Scheme 1. Strategies for the photo-induced ring-opening functionalizations of cyclic iminyl radicals. (A) Previous work: photoredox ring-opening functionalizations. (B) Photoredox strategies for radical ring-opening C–C bond formation. (C) This work: photoredox-Ni ring-opening arylations, vinylations and alkylations.
Scheme 2
Scheme 2. Proposed dual photoredox-Ni catalytic cycle for the radical ring-opening-arylation cascades.
Scheme 3
Scheme 3. Development of dual photoredox–Ni ring-opening-arylation process.
Scheme 4
Scheme 4. Scope of the dual photoredox–Ni ring-opening-arylation process.
Scheme 5
Scheme 5. Development of dual photoredox–Ni ring-opening-vinylation process.
Scheme 6
Scheme 6. Scope of the dual photoredox–Ni ring-opening-vinylation process.
Scheme 7
Scheme 7. Development of dual photoredox–Ni ring-opening-alkylation process.
Scheme 8
Scheme 8. Scope of the dual photoredox–Ni ring-opening-alkylation process.
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