Asymmetric copper-catalyzed C-N cross-couplings induced by visible light

Science

Volumn 351, Issue 6274, 2016, Pages 681-684

  Kainz, Quirin M ^a   Matier, Carson D ^a   Bartoszewicz, Agnieszka ^a   Zultanski, Susan L ^a   Peters, Jonas C ^a   Fu, Gregory C ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; COPPER; ELECTROPHILE; NITROGEN; TRANSITION ELEMENT;

ASYMMETRY; CATALYSIS; COPPER; LIGHT INTENSITY; PHOTOCHEMISTRY; TEMPERATURE EFFECT; TRANSITION ELEMENT; VISIBLE SPECTRUM;

ALKYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL BOND; ENANTIOMER; ENANTIOSELECTIVITY; LIGHT; PRIORITY JOURNAL; RACEMIC MIXTURE;

EID: 84957899492     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.aad8313     Document Type: Article

References (29)

1. A. Albini, M. Fagnoni, Photochemically-Generated Intermediates in Synthesis (Wiley, 2013).
2. C. K. Prier, D. A. Rankic, D. W. C. MacMillan, Chem. Rev. 113, 5322-5363 (2013).
3. R. Brimioulle, D. Lenhart, M. M. Maturi, T. Bach, Angew. Chem. Int. Ed. 54, 3872-3890 (2015).
4. D. M. Schultz, T. P. Yoon, Science 343, 1239176 (2014).
5. H. Huo et al., Nature 515, 100-103 (2014).
6. H. Huo, C. Wang, K. Harms, E. Meggers, J. Am. Chem. Soc. 137, 9551-9554 (2015).
7. C. Wang et al., Chemistry 21, 7355-7359 (2015).
8. A. Bauer, F. Westkämper, S. Grimme, T. Bach, Nature 436, 1139-1140 (2005).
9. D. A. Nicewicz, T. M. Nguyen, ACS Catal. 4, 355-360 (2014).
10. S. E. Creutz, K. J. Lotito, G. C. Fu, J. C. Peters, Science 338, 647-651 (2012).
11. S. A. Lawrence, Amines: Synthesis, Properties and Applications (Cambridge Univ. Press, 2004).
12. L. Jiang, S. L. Buchwald, in Metal-Catalyzed Cross-Coupling Reactions, A. de Meijere, F. Diederich, Eds. (vol. 2, Wiley-VCH, 2004), pp. 699-760.
13. J. F. Hartwig, S. Shekhar, Q. Shen, F. Barrios-Landeros, in Chemistry of Anilines, Z. Rappoport, Ed. (vol. 1, Wiley, 2007), pp. 455-536.
14. A. C. Bissember, R. J. Lundgren, S. E. Creutz, J. C. Peters, G. C. Fu, Angew. Chem. Int. Ed. 52, 5129-5133 (2013).
15. H.-Q. Do, S. Bachman, A. C. Bissember, J. C. Peters, G. C. Fu, J. Am. Chem. Soc. 136, 2162-2167 (2014).
16. S. Paria, O. Reiser, ChemCatChem 6, 2477-2483 (2014).
17. C. Fischer, G. C. Fu, J. Am. Chem. Soc. 127, 4594-4595 (2005).
18. Y. Liang, G. C. Fu, . J. Am. Chem. Soc. 137, 9523-9526 (2015).
19. M. Jin, L. Adak, M. Nakamura, J. Am. Chem. Soc. 137, 7128-7134 (2015).
20. K. W. Quasdorf, L. E. Overman, Nature 516, 181-191 (2014).
21. C. Schuster et al., J. Org. Chem. 80, 5666-5673 (2015).
22. A. W. Schmidt, K. R. Reddy, H.-J. Knölker, Chem. Rev. 112, 3193-3328 (2012).
23. D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. Int. Ed. Engl. 34, 1059-1070 (1995).
24. P. M. Lundin, G. C. Fu, J. Am. Chem. Soc. 132, 11027-11029 (2010).
25. S. Balasubramaniam, I. S. Aidhen, Synthesis 2008, 3707-3738 (2008).
26. G. W. Gribble, Ed., Heterocyclic Scaffolds II: Reactions and Applications of Indoles (Springer, 2010).
27. R. Vallakati, J. A. May, J. Am. Chem. Soc. 134, 6936-6939 (2012).
28. E. K. Schmitt et al., Angew. Chem. Int. Ed. 50, 5889-5891 (2011).
29. H. Pellissier, in Separation of Enantiomers, M. Todd, Ed. (Wiley-VCH, 2014), pp. 75-122.