1. Asymmetric copper-catalyzed C-N cross-couplings induced by visible light
by Quirin M. Kainz, Carson D. Matier, Agnieszka Bartoszewicz, Susan L. Zultanski, Jonas C. Peters, and Gregory C. Fu
Science
Volume 351(6274):
February 12, 2016
Published by AAAS

2. Fig. 1 A photocatalytic approach to the asymmetric synthesis of amines.
A photocatalytic approach to the asymmetric synthesis of amines. (A) Asymmetric copper-catalyzed C-N cross-couplings induced by visible light (cat., catalyst; hν, light energy; Ph, phenyl). (B) Outline of a strategy for the enantioconvergent cross-coupling of a racemic tertiary alkyl halide via a radical intermediate.
Quirin M. Kainz et al. Science 2016;351:
Published by AAAS

3. Fig. 2 Asymmetric copper-catalyzed C-N cross-couplings induced by visible light.
Asymmetric copper-catalyzed C-N cross-couplings induced by visible light. (A) Effect of changes in the reaction parameters. Yields were determined through analysis by proton nuclear magnetic resonance (1H NMR) spectroscopy with the aid of an internal standard. (B) Scope of the reaction with respect to the electrophile. Yields were determined by isolation after chromatographic purification. (C) Scope of the reaction with respect to the nucleophile. Yields were determined by isolation after chromatographic purification. Et, ethyl group; Bn, benzyl group; Me, methyl group; t-Bu, tert-butyl group.
Quirin M. Kainz et al. Science 2016;351:
Published by AAAS

4. Fig. 3 Mechanistic studies.
Mechanistic studies. (A) Investigation of kinetic resolution. (B) Outline of a possible pathway for photoinduced copper-catalyzed C-N cross-couplings of alkyl halides. For simplicity, all copper complexes are illustrated as neutral species, and all processes are depicted as being irreversible; X may be serving as an inner- or an outer-sphere ligand [Ln denotes additional ligand(s) coordinated to copper]. (C) Synthesis and structural characterization of (L*)2Cu(carbazolide) (thermal ellipsoids are drawn at 50% probability, and H atoms are omitted for clarity). (D) Stoichiometric cross-coupling reaction with isolated (L*)2Cu(carbazolide).
Quirin M. Kainz et al. Science 2016;351:
Published by AAAS