Radical Umpolung: Efficient Options for the Synthesis of 1,4-Dicarbonyl Compounds
Corresponding Author
Dr. Xiang-Yu Chen
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
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Prof. Dr. Dieter Enders
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Search for more papers by this authorCorresponding Author
Dr. Xiang-Yu Chen
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Dieter Enders
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Search for more papers by this authorGraphical Abstract
Radical developments: Photochemical/secondary amine dual catalysis has proven to be an efficient strategy for radical umpolung reactions. Two new processes provide an elegant solution to a long-standing chemoselectivity problem for the synthesis of 1,4-dicarbonyl compounds.
References
- 1
- 1aP. S. Baran, M. P. DeMartino, Angew. Chem. Int. Ed. 2006, 45, 7083; Angew. Chem. 2006, 118, 7241;
- 1bE. E. Robinson, R. J. Thomson, J. Am. Chem. Soc. 2018, 140, 1956;
- 1cD. Kaldre, I. Klose, N. Maulide, Science 2018, 361, 664;
- 1dH.-Y. Jang, J.-B. Hong, D. W. C. MacMillan, J. Am. Chem. Soc. 2007, 129, 7004;
- 1eS. Huang, L. Kötzner, C. K. De, B. List, J. Am. Chem. Soc. 2015, 137, 3446.
- 2D. Seebach, Angew. Chem. Int. Ed. Engl. 1979, 18, 239; Angew. Chem. 1979, 91, 259.
- 3
- 3aY. Wu, L. Hu, Z. Li, L. Deng, Nature 2015, 523, 445;
- 3bJ. Chen, X. Gong, J. Li, Y. Li, J. Ma, C. Hou, G. Zhao, W. Yuan, B. Zhao, Science 2018, 360, 1438.
- 4
- 4aD. Enders, P. Müller, D. Klein, Synlett 1998, 43;
- 4bD. Enders, U. Baus, P. Müller, K. C. Nicolaou, B. Jandeleit, Mol. Online 1998, 2, 15.
- 5
- 5aD. Enders, P. Gerdes, H. Kipphardt, Angew. Chem. Int. Ed. Engl. 1990, 29, 179; Angew. Chem. 1990, 102, 226;
- 5bD. Enders, J. P. Shilvock, Chem. Soc. Rev. 2000, 29, 359.
- 6H. Stetter, M. Schreckenberg, Angew. Chem. Int. Ed. Engl. 1973, 12, 81; Angew. Chem. 1973, 85, 89.
- 7
- 7aJ. Tiebes, Diploma Thesis, RWTH Aachen, 1990;
- 7bD. Enders, K. Breuer, J. Runsink, J. H. Teles, Helv. Chim. Acta 1996, 79, 1899.
- 8
- 8aD. Enders, J. Han, A. Henseler, Chem. Commun. 2008, 3989;
- 8bQ. Liu, S. Perreault, T. Rovis, J. Am. Chem. Soc. 2008, 130, 14066;
- 8cT. Jousseaume, N. E. Wurz, F. Glorius, Angew. Chem. Int. Ed. 2011, 50, 1410; Angew. Chem. 2011, 123, 1446.
- 9
- 9aA. Banerjee, Z. Lei, M.-Y. Ngai, Synthesis 2019, 51, 303;
- 9bC. Raviola, S. Protti, D. Ravelli, M. Fagnoni, Green Chem. 2019, 21, 748.
- 10T. Morack, C. Mück-Lichtenfeld, R. Gilmour, Angew. Chem. Int. Ed. 2019, 58, 1208; Angew. Chem. 2019, 131, 1221.
- 11G. Goti, B. Bieszczad, A. Vega-Peñaloza, P. Melchiorre, Angew. Chem. Int. Ed. 2019, 58, 1213; Angew. Chem. 2019, 131, 1226.
- 12L. Buzzetti, A. Prieto, S. R. Roy, P. Melchiorre, Angew. Chem. Int. Ed. 2017, 56, 15039; Angew. Chem. 2017, 129, 15235.
- 13J.-J. Zhao, H.-H. Zhang, X. Shen, S. Yu, Org. Lett. 2019, 21, 913.
