Download PDF
König, B.: 2019 Science of Synthesis, 2018/6: Photocatalysis in Organic Synthesis DOI: 10.1055/sos-SD-229-00133
Photocatalysis in Organic Synthesis

7 Organocatalysis with Amines in Photocatalysis

More Information

Book

Editor: König, B.

Authors: Akita, M.; Albero, J.; Amador, A. G.; Ashley, M. A.; Brasholz, M.; Corcé, V.; DiRocco, D. A.; Dix, S.; Ehrnsberger, P.; Fensterbank, L.; Gaida, F.; García, H.; Ghosh, I.; Gilmour, R.; Griesbeck, A. G.; Gutiérrez Bonet, Á.; Hepburn, H. B.; Hopkinson, M. N.; Kelly, C. B.; Koike, T.; Laha, R.; Lang, S. B.; Leonori, D.; Lévêque, C.; Li, P.; Lu, L.-Q.; Matsui, J. K.; Melchiorre, P.; Metternich, J. B.; Molander, G. A.; Mudd, R. J.; Ollivier, C.; Pandey, G.; Phelan, J. P.; Reiser, O.; Rey, Y. P.; Rovis, T.; Ruffoni, A.; Scholz, S. O.; Schultz, D. M.; Skubi, K. L.; Speckmeier, E.; Thullen, S. M.; Vollmer, M.; Wang, L.; Wang, M.; Wei, Y.; Xiao, W.-J.; Yoon, T. P.; Zeitler, K.; Zhou, Q.-Q.

Title: Photocatalysis in Organic Synthesis

Print ISBN: 9783132417021; Online ISBN: 9783132417069; Book DOI: 10.1055/b-006-161273

1st edition © 2019. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

Also available at
 


Abstract

This chapter details recent advances in enantioselective amine-catalyzed reactions triggered by light. By presenting a selection of pioneering studies, the chapter highlights how the combination of photochemistry and amine-mediated catalysis has created exciting new opportunities in asymmetric synthesis while profoundly influencing different fields of modern chemical research, such as radical reactivity. The discussion focuses on the concepts of enamine and iminium ion mediated reactions and their combination with photochemical reactivity. The selected methods represent the state of the art in the rapidly evolving area of photochemical amine-catalyzed processes, which provides effective synthetic tools for making chiral molecules sustainably.

Key words

photocatalysis - amines - asymmetric catalysis - enamines - iminium ions - electron transfer - organocatalysis - radical reactivity - photochemistry - redox processes
 
  • 1 Melchiorre P, Marigo M, Carlone A, Bartoli G. Angew. Chem. 2008; 120: 6232 Angew. Chem. Int. Ed. 2008; 47: 6138
  • 2 Donslund BS, Johansen TK, Poulsen PH, Halskov KS, Jørgensen KA. Angew. Chem. 2015; 127: 14066 Angew. Chem. Int. Ed. 2015; 54: 13860
  • 3 Lelais G, MacMillan DWC. Aldrichimica Acta 2006; 39: 79
  • 4 Melchiorre P. Angew. Chem. 2012; 124: 9886 Angew. Chem. Int. Ed. 2012; 51: 9748
  • 5 MacMillan DWC. Nature (London) 2008; 455: 304
  • 6 List B. Angew. Chem. 2010; 122: 1774 Angew. Chem. Int. Ed. 2010; 49: 1730
  • 7 Schultz DM, Yoon TP. Science (Washington, D. C.) 2014; 343: 1239 176
  • 8 Silvi M, Melchiorre P. Nature (London) 2018; 554: 41
  • 9 Curran DP, Porter NA, Giese B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications. VCH; Weinheim, Germany 1996
    Google Scholar
  • 10 Brimioulle R, Lenhart D, Maturi MM, Bach T. Angew. Chem. 2015; 127: 3944 Angew. Chem. Int. Ed. 2015; 54: 3872
  • 11 Shaw MH, Twilton J, MacMillan DWC. J. Org. Chem. 2016; 81: 6898
  • 12 Beeson TD, Mastracchio A, Hong J.-B, Ashton K, MacMillan DWC. Science (Washington, D. C.) 2007; 316: 582
  • 13 Melchiorre P. Angew. Chem. 2009; 121: 1386 Angew. Chem. Int. Ed. 2009; 48: 1360
  • 14 Nicewicz DA, MacMillan DWC. Science (Washington, D. C.) 2008; 322: 77
  • 15 Giese B. Radicals in Organic Synthesis: Formation of Carbon–Carbon Bonds. Pergamon; Oxford 1986
    Google Scholar
  • 16 Cismesia MA, Yoon TP. Chem. Sci. 2015; 6: 5426
  • 17 Neumann M, Füldner S, König B, Zeitler K. Angew. Chem. 2011; 123: 981 Angew. Chem. Int. Ed. 2011; 50: 951
  • 18 Cherevatskaya M, Neumann M, Füldner S, Harlander C, Kümmel S, Dankesreiter S, Pfitzner A, Zeitler K, König B. Angew. Chem. 2012; 124: 4138 Angew. Chem. Int. Ed. 2012; 51: 4062
  • 19 Riente P, Adams AM, Albero J, Palomares E, Pericàs MA. Angew. Chem. 2014; 126: 9767 Angew. Chem. Int. Ed. 2014; 53: 9613
  • 20 Gualandi A, Marchini M, Mengozzi L, Natali M, Lucarini M, Ceroni P, Cozzi PG. ACS Catal. 2015; 5: 5927
  • 21 Nagib DA, Scott ME, MacMillan DWC. J. Am. Chem. Soc. 2009; 131: 10875
  • 22 Shih H.-W, Vander Wal MN, Grange RL, MacMillan DWC. J. Am. Chem. Soc. 2010; 132: 13600
  • 23 Welin ER, Warkentin AA, Conrad JC, MacMillan DWC. Angew. Chem. 2015; 127: 9804 Angew. Chem. Int. Ed. 2015; 54: 9668
  • 24 Zhu Y, Zhang L, Luo S. J. Am. Chem. Soc. 2014; 136: 14642
  • 25 MacMillan DWC, Beeson TD. Science of Synthesis: Asymmetric Organocatalysis 2012; 1: 271
  • 26 Seebach D. Angew. Chem. 1979; 91: 259 Angew. Chem. Int. Ed. Engl. 1979; 18: 239
  • 27 Capacci AG, Malinowski JT, McAlpine NJ, Kuhne J, MacMillan DWC. Nat. Chem. 2017; 9: 1073
  • 28 Mayer JM. Acc. Chem. Res. 2011; 44: 36
  • 29 Mulliken RS. J. Am. Chem. Soc. 1952; 74: 811
  • 30 Arceo E, Jurberg ID, Álvarez-Fernández A, Melchiorre P. Nat. Chem. 2013; 5: 750
  • 31 Silvi M, Arceo E, Jurberg ID, Cassani C, Melchiorre P. J. Am. Chem. Soc. 2015; 137: 6120
  • 32 Bahamonde A, Melchiorre P. J. Am. Chem. Soc. 2016; 138: 8019
  • 33 Filippini G, Silvi M, Melchiorre P. Angew. Chem. 2017; 129: 4518 Angew. Chem. Int. Ed. 2017; 56: 4447
  • 34 Studer A, Curran DP. Angew. Chem. 2016; 128: 58 Angew. Chem. Int. Ed. 2016; 55: 58
  • 35 Catalytic Asymmetric Conjugate Reactions. Córdova A. Wiley VCH; Weinheim, Germany 2010
    Google Scholar
  • 36 Pirnot MT, Rankic DA, Martin DBC, MacMillan DWC. Science (Washington, D. C.) 2013; 339: 1593
  • 37 Murphy JJ, Bastida D, Paria S, Fagnoni M, Melchiorre P. Nature (London) 2016; 532: 218
  • 38 Silvi M, Verrier C, Rey YP, Buzzetti L, Melchiorre P. Nat. Chem. 2017; 9: 868
  • 39 Petronijević FR, Nappi M, MacMillan DWC. J. Am. Chem. Soc. 2013; 135: 18323
  • 40 Jeffrey JL, Petronijević FR, MacMillan DWC. J. Am. Chem. Soc. 2015; 137: 8404
  • 41 Terrett JA, Clift MD, MacMillan DWC. J. Am. Chem. Soc. 2014; 136: 6858
  • 42 Quasdorf KW, Overman LE. Nature (London) 2014; 516: 181
  • 43 Jakobsen HJ, Lawesson S.-O, Marshall JTB, Schroll G, Williams DH. J. Chem. Soc. B 1966; 940
  • 44 Bahamonde A, Murphy JJ, Savarese M, Brémond E, Cavalli A, Melchiorre P. J. Am. Chem. Soc. 2017; 139: 4559
  • 45 Verrier C, Alandini N, Pezzetta C, Moliterno M, Buzzetti L, Hepburn HB, Vega-Peñaloza A, Silvi M, Melchiorre P. ACS Catal. 2018; 8: 1062
  • 46 Woźniak Ł, Magagnano G, Melchiorre P. Angew. Chem. 2018; 130: 1080 Angew. Chem. Int. Ed. 2018; 57: 1068