Download PDF
Molander, G. A.: 2020 Science of Synthesis, 2019/5: Dual Catalysis in Organic Synthesis 2 DOI: 10.1055/sos-SD-232-00119
Dual Catalysis in Organic Synthesis 2

2.4 Organocatalyst/Photocatalyst Dual Catalysis

More Information

Book

Editor: Molander, G. A.

Authors: Bäckvall, J.-E.; Cruz, F. A.; Deng, Y.-H.; Diéguez, M.; Dong, V. M.; Galman, J. L.; Gröger, H. ; Montgomery, S. L.; Pàmies, O.; Parmeggiani, F.; Shao, Z.; Shi, X.; Turner, N. J.; Vitale, M. R. ; Wang, H.-Y.; Wang, J.; Yamashita, Y.; Zeitler, K. ; Zhao, G.

Title: Dual Catalysis in Organic Synthesis 2

Print ISBN: 978313242981-9; Online ISBN: 978313242985-7; Book DOI: 10.1055/b-006-166041

2020 © 2020 Georg Thieme Verlag KG
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

Recent advances in dual-catalytic methods combining organocatalysis with (visible-light) photocatalysis are detailed within this chapter. It summarizes general aspects together with selected state-of-the-art procedures, highlighting both pioneering examples and current developments.

The merger of organocatalysis with photocatalysis has proven to be enormously powerful, not only because it provides a synthetic platform to readily access radical intermediates within an organocatalytic manifold and its potential to alter the reactivity of typical organocatalytic intermediates, but also due to the new opportunities in asymmetric synthesis. The synergistic dual combination with organocatalysis enables photocatalytic reactions to be conducted in an enantioselective fashion and thereby has had a profound influence on several fields of current chemical research, including radical chemistry.

Key words

dual catalysis - organocatalysis - photocatalysis - photoredox catalysis - visible light - asymmetric catalysis - aminocatalysis - enamines - iminium ions - ammonium enolates - isothioureas - N-heterocyclic carbene (NHC) catalysis - Brønsted acid catalysis - chiral phosphoric acids (CPA) - hydrogen-bonding catalysis - thioureas - amidinium - radicals - single-electron transfer (SET) - proton-coupled electron transfer (PCET) - hydrogen-atom transfer (HAT) - radical reactions - ketyl radicals - thiyl radicals - arylation - amination - alkylation - C-H functionalization - activation of C-H bonds - umpolung
 
  • 1 A. Berkessel,, H. Gröger,. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis. Wiley-VCH; Weinheim, Germany 2005
    Google Scholar
  • 3 Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications Dalko, P. I., Ed.; Wiley-VCH: Weinheim, Germany (2013).
  • 4 D. W. C. MacMillan,. Nature (London). 2008; 455: 304
    Google Scholar
  • 5 Science of Synthesis: Asymmetric Organocatalysis List, B., Ed.; Thieme: Stuttgart (2012); Vol. 1.
  • 6 Science of Synthesis: Asymmetric Organocatalysis Maruoka, K., Ed.; Thieme: Stuttgart (2012); Vol. 2.
  • 7 C. K. Prier,, D. A. Rankic,, D. W. C. MacMillan,. Chem. Rev.. 2013; 113: 5322
    Google Scholar
  • 9 N. A. Romero,, D. A. Nicewicz,. Chem. Rev.. 2016; 116: 10075
    Google Scholar
  • 10 Visible Light Photocatalysis in Organic Chemistry Stephenson, C. R. J. Yoon, T. P. MacMillan, D. W. C., Eds.; Wiley-VCH: Weinheim, Germany (2018).
  • 11 J. K. Matsui,, S. B. Lang,, D. R. Heitz,, G. A. Molander,. ACS Catal.. 2017; 7: 2563
    Google Scholar
  • 12 Zeitler, K. Neumann, M., In Chemical PhotocatalysisKönig, B., Ed.; de Gruyter: Berlin (2013); p 151.
  • 13 M. N. Hopkinson,, B. Sahoo,, J.-L. Li,, F. Glorius,. Chem.–Eur. J.. 2014; 20: 3874
    Google Scholar
  • 14 K. L. Skubi,, T. R. Blum,, T. P. Yoon,. Chem. Rev.. 2016; 116: 10035
    Google Scholar
  • 15 J. Twilton,, C. C. Le,, P. Zhang,, M. H. Shaw,, R. W. Evans,, D. W. C. MacMillan,. Nat. Rev. Chem.. 2017; 1: 0052
    Google Scholar
  • 16 J. Seayad,, B. List,. Org. Biomol. Chem.. 2005; 3: 719
    Google Scholar
  • 17 Science of Synthesis: Photocatalysis in Organic SynthesisKönig, B., Ed.; Thieme: Stuttgart (2019).
  • 18 K. Zeitler,. Angew. Chem. Int. Ed.. 2009; 48: 9785
    Google Scholar
  • 19 M. H. Shaw,, J. Twilton,, D. W. C. MacMillan,. J. Org. Chem.. 2016; 81: 6898
    Google Scholar
  • 20 F. Strieth-Kalthoff,, M. J. James,, M. Teders,, L. Pitzer,, F. Glorius,. Chem. Soc. Rev.. 2018; 47: 7190
    Google Scholar
  • 21 Q.-Q. Zhou,, Y.-Q. Zou,, L.-Q. Lu,, W.-J. Xiao,. Angew. Chem. Int. Ed.. 2019; 58: 1586
    Google Scholar
  • 22 S. Protti,, M. Fagnoni,, D. Ravelli,. ChemCatChem. 2015; 7: 1516
    Google Scholar
  • 23 L. Capaldo,, D. Ravelli,. Eur. J. Org. Chem.. 2017; 2056
    Google Scholar
  • 24 Zeitler, K., In Visible Light Photocatalysis in Organic ChemistryStephenson, C. R. J. Yoon, T. P. MacMillan, D. W. C., Eds.; Wiley-VCH: Weinheim, Germany (2018); p 159.
  • 25 R. Brimioulle,, D. Lenhart,, M. M. Maturi,, T. Bach,. Angew. Chem. Int. Ed.. 2015; 54: 3872
    Google Scholar
  • 26 E. Meggers,. Chem. Commun. (Cambridge). 2015; 51: 3290
    Google Scholar
  • 27 M. Silvi,, P. Melchiorre,. Nature (London). 2018; 554: 41
    Google Scholar
  • 28 M. E. Abbasov,, D. Romo,. Nat. Prod. Rep.. 2014; 31: 1318
    Google Scholar
  • 29 D. Kampen,, C. M. Reisinger,, B. List,. Top. Curr. Chem.. 2010; 291: 395
    Google Scholar
  • 30 E. Arceo,, I. D. Jurberg,, A. Álvarez-Fernández,, P. Melchiorre,. Nat. Chem.. 2013; 5: 750
    Google Scholar
  • 31 C. G. S. Lima,, de M. Lima , M. Duarte,, I. D. Jurberg,, M. W. Paixão,. ACS Catal.. 2016; 6: 1389
    Google Scholar
  • 32 Z.-Y. Cao,, T. Ghosh,, P. Melchiorre,. Nat. Commun.. 2018; 9: 3274
    Google Scholar
  • 33 A. A. Ghogare,, A. Greer,. Chem. Rev.. 2016; 116: 9994
    Google Scholar
  • 34 P. Melchiorre,, M. Marigo,, A. Carlone,, G. Bartoli,. Angew. Chem. Int. Ed.. 2008; 47: 6138
    Google Scholar
  • 35 S. Bertelsen,, K. A. Jørgensen,. Chem. Soc. Rev.. 2009; 38: 2178
    Google Scholar
  • 36 S. France,, D. J. Guerin,, S. J. Miller,, T. Lectka,. Chem. Rev.. 2003; 103: 2985
    Google Scholar
  • 37 B. S. Donslund,, T. K. Johansen,, P. H. Poulsen,, K. S. Halskov,, K. A. Jørgensen,. Angew. Chem. Int. Ed.. 2015; 54: 13860
    Google Scholar
  • 38 G. J. Reyes-Rodríguez,, N. M. Rezayee,, A. Vidal-Albalat,, K. A. Jørgensen,. Chem. Rev.. 2019; 119: 4221
    Google Scholar
  • 39 G. Lelais,, D. W. C. MacMillan,. Aldrichimica Acta. 2006; 39: 79
    Google Scholar
  • 40 Mahrwald, R., In Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and ApplicationsDalko, P. I., Ed.; Wiley-VCH: Weinheim, Germany (2013); p 69.
  • 41 P. Melchiorre,. Angew. Chem. Int. Ed.. 2012; 51: 9748
    Google Scholar
  • 42 L. Jiang,, Y.-C. Chen,. Catal. Sci. Technol.. 2011; 1: 354
    Google Scholar
  • 43 A. Vega-Peñaloza,, S. Paria,, M. Bonchio,, L. DellʼAmico,, X. Companyó,. ACS Catal.. 2019; 9: 6058
    Google Scholar
  • 44 S. Mukherjee,, J. W. Yang,, S. Hoffmann,, B. List,. Chem. Rev.. 2007; 107: 5471
    Google Scholar
  • 46 A. Erkkilä,, I. Majander,, P. M. Pihko,. Chem. Rev.. 2007; 107: 5416
    Google Scholar
  • 47 M. J. Gaunt,, C. C. C. Johansson,. Chem. Rev.. 2007; 107: 5596
    Google Scholar
  • 48 MacMillan, D. W. C. Rendler, S., In Asymmetric Synthesis II: More Methods and ApplicationsChristmann, M. Bräse, S., Eds.; Wiley-VCH: Weinheim, Germany (2012); p 87.
  • 49 M. Mečiarová,, P. Tisovský,, R. Šebesta,. New J. Chem.. 2016; 40: 4855
    Google Scholar
  • 50 D. A. Nicewicz,, D. W. C. MacMillan,. Science (Washington, D. C.). 2008; 322: 77
    Google Scholar
  • 51 A. Juris,, V. Balzani,, F. Barigelletti,, S. Campagna,, P. Belser,, A. Von Zelewsky,. Coord. Chem. Rev.. 1988; 84: 85
    Google Scholar
  • 52 M. A. Cismesia,, T. P. Yoon,. Chem. Sci.. 2015; 6: 5426 Chem. Sci.. 2015; 6: 6019
    Google Scholar
  • 53 L. Buzzetti,, G. E. M. Crisenza,, P. Melchiorre,. Angew. Chem. Int. Ed.. 2019; 58: 3730
    Google Scholar
  • 54 A. Studer,, D. Curran,. Angew. Chem. Int. Ed.. 2016; 55: 58
    Google Scholar
  • 55 P. Riente,, A. M. Adams,, J. Albero,, E. Palomares,, M. A. Pericàs,. Angew. Chem. Int. Ed.. 2014; 53: 9613
    Google Scholar
  • 56 M. Cherevatskaya,, M. Neumann,, S. Füldner,, C. Harlander,, S. Kümmel,, S. Dankesreiter,, A. Pfitzner,, K. Zeitler,, B. König,. Angew. Chem. Int. Ed.. 2012; 51: 4062
    Google Scholar
  • 57 P. Wu,, C. He,, J. Wang,, X. Peng,, X. Li,, Y. An,, C. Duan,. J. Am. Chem. Soc.. 2012; 134: 14991
    Google Scholar
  • 58 A. Gualandi,, M. Marchini,, L. Mengozzi,, M. Natali,, M. Lucarini,, P. Ceroni,, P. G. Cozzi,. ACS Catal.. 2015; 5: 5927
    Google Scholar
  • 59 M. Neumann,, S. Füldner,, B. König,, K. Zeitler,. Angew. Chem. Int. Ed.. 2011; 50: 951
    Google Scholar
  • 60 Hari, D. H. König, B. Chem. Commun. (Cambridge) (2014) 506688.
  • 61 Srivastava, V. Singh, P. P. RSC Adv. (2017) 731377.
  • 62 M. Majek,, F. Filace,, A. Jacobi von Wangelin,. Beilstein J. Org. Chem.. 2014; 10: 981
    Google Scholar
  • 63 K. Fidaly,, C. Ceballos,, A. Falguières,, M. S.-I. Veitia,, A. Guy,, C. Ferroud,. Green Chem.. 2012; 14: 1293
    Google Scholar
  • 64 M. Silvi,, E. Arceo,, I. D. Jurberg,, C. Cassani,, P. Melchiorre,. J. Am. Chem. Soc.. 2015; 137: 6120
    Google Scholar
  • 65 Speckmeier, E. Zeitler, K., In Science of Synthesis: Photocatalysis in Organic SynthesisKönig, B., Ed.; Thieme: Stuttgart (2019); p 101.
  • 66 D. Cambié,, C. Bottecchia,, N. J. W. Straathof,, V. Hessel,, T. Noël,. Chem. Rev.. 2016; 116: 10276
    Google Scholar
  • 67 M. B. Plutschack,, B. Pieber,, K. Gilmore,, P. H. Seeberger,. Chem. Rev.. 2017; 117: 11796
    Google Scholar
  • 68 M. Neumann,, K. Zeitler,. Org. Lett.. 2012; 14: 2658
    Google Scholar
  • 69 E. R. Welin,, A. A. Warkentin,, J. C. Conrad,, D. W. C. MacMillan,. Angew. Chem. Int. Ed.. 2015; 54: 9668
    Google Scholar
  • 70 D. A. Nagib,, M. E. Scott,, D. W. C. MacMillan,. J. Am. Chem. Soc.. 2009; 131: 10875
    Google Scholar
  • 71 H.-W. Shih,, M. N. Vander Wal,, R. L. Grange,, D. W. C. MacMillan,. J. Am. Chem. Soc.. 2010; 132: 13600
    Google Scholar
  • 72 G. Cecere,, C. M. König,, J. L. Alleva,, D. W. C. MacMillan,. J. Am. Chem. Soc.. 2013; 135: 11521
    Google Scholar
  • 73 E. Larionov,, M. M. Mastandrea,, M. A. Pericàs,. ACS Catal.. 2017; 7: 7008
    Google Scholar
  • 75 A. G. Capacci,, J. T. Malinowski,, N. J. McAlpine,, J. Kuhne,, D. W. C. MacMillan,. Nat. Chem.. 2017; 9: 1073
    Google Scholar
  • 76 Y. Zhu,, L. Zhang,, S. Luo,. J. Am. Chem. Soc.. 2014; 136: 14642
    Google Scholar
  • 78 J. W. Beatty,, C. R. J. Stephenson,. Acc. Chem. Res.. 2015; 48: 1474
    Google Scholar
  • 79 Zou, Y.-Q. Xiao, W.-J., In Visible Light Photocatalysis in Organic ChemistryStephenson, C. R. J. Yoon, T. P. MacMillan, D. W. C., Eds.; Wiley-VCH: Weinheim, Germany (2018); p 93.
  • 80 M. Rueping,, C. Vila,, R. M. Koenigs,, K. Poscharny,, D. C. Fabry,. Chem. Commun. (Cambridge). 2011; 47: 2360
    Google Scholar
  • 81 M. Rueping,, J. Zoller,, D. C. Fabry,, K. Poscharny,, R. M. Koenigs,, T. E. Weirich,, J. Mayer,. Chem.–Eur. J.. 2012; 18: 3478
    Google Scholar
  • 82 Q. Yang,, L. Zhang,, C. Ye,, S. Luo,, L.-Z. Wu,, C.-H. Tung,. Angew. Chem. Int. Ed.. 2017; 56: 3694
    Google Scholar
  • 83 H. Hou,, S. Zhu,, I. Atodiresei,, M. Rueping,. Eur. J. Org. Chem.. 2018; 1277
    Google Scholar
  • 84 M. T. Pirnot,, D. A. Rankic,, D. B. C. Martin,, D. W. C. MacMillan,. Science (Washington, D. C.). 2013; 339: 1593
    Google Scholar
  • 85 D. Leifert,, A. Studer,. Angew. Chem. Int. Ed.. 2019; 58
    Google Scholar
  • 86 F. R. Petronijević,, M. Nappi,, D. W. C. MacMillan,. J. Am. Chem. Soc.. 2013; 135: 18323
    Google Scholar
  • 87 J. L. Jeffrey,, F. R. Petronijević,, D. W. C. MacMillan,. J. Am. Chem. Soc.. 2015; 137: 8404
    Google Scholar
  • 88 J. A. Terrett,, M. D. Clift,, D. W. C. MacMillan,. J. Am. Chem. Soc.. 2014; 136: 6858
    Google Scholar
  • 89 J. J. Murphy,, D. Bastida,, S. Paria,, M. Fagnoni,, P. Melchiorre,. Nature (London). 2016; 532: 218
    Google Scholar
  • 90 A. Bahamonde,, J. J. Murphy,, M. Savarese,, E. Brémond,, A. Cavalli,, P. Melchiorre,. J. Am. Chem. Soc.. 2017; 139: 4559
    Google Scholar
  • 91 M. Silvi,, C. Verrier,, Y. P. Rey,, L. Buzzetti,, P. Melchiorre,. Nat. Chem.. 2017; 9: 868
    Google Scholar
  • 92 G. Goti,, B. Bieszczad,, A. Vega-Peñaloza,, P. Melchiorre,. Angew. Chem. Int. Ed.. 2019; 58: 1213
    Google Scholar
  • 93 T. Morack,, C. Mück-Lichtenfeld,, R. Gilmour,. Angew. Chem. Int. Ed.. 2019; 58: 1208
    Google Scholar
  • 94 J.-J. Zhao,, H.-H. Zhang,, X. Shen,, S. Yu,. Org. Lett.. 2019; 21: 913
    Google Scholar
  • 95 Z.-J. Feng,, J. Xuan,, X.-D. Xia,, W. Ding,, W. Guo,, J.-R. Chen,, Y.-Q. Zou,, L.-Q. Lu,, W.-J. Xiao,. Org. Biomol. Chem.. 2014; 12: 2037
    Google Scholar
  • 96 G. Wei,, C. Zhang,, F. Bureš,, X. Ye,, C.-H. Tan,, Z. Jiang,. ACS Catal.. 2016; 6: 3708
    Google Scholar
  • 97 L. C. Morrill,, A. D. Smith,. Chem. Soc. Rev.. 2014; 43: 6214
    Google Scholar
  • 98 J. Merad,, J.-M. Pons,, O. Chuzel,, C. Bressy,. Eur. J. Org. Chem.. 2016; 5589
    Google Scholar
  • 99 J. N. Arokianathar,, A. B. Frost,, A. M. Z. Slawin,, D. Stead,, A. D. Smith,. ACS Catal.. 2018; 8: 1153
    Google Scholar
  • 100 D. M. Flanigan,, F. Romanov-Michailidis,, N. A. White,, T. Rovis,. Chem. Rev.. 2015; 115: 9307
    Google Scholar
  • 101 K. Zeitler,. Angew. Chem. Int. Ed.. 2005; 44: 7506
    Google Scholar
  • 102 Davies, A. T. Smith, A. D., In Science of Synthesis: N-Heterocyclic Carbenes in Catalytic Organic Synthesis Nolan, S. P. Cazin, C. S. J., Eds.; Thieme: Stuttgart (2018); Vol. 2, p 395.
  • 103 N-Heterocyclic Carbenes in Organocatalysis Biju, A. T.; Ed.; Wiley-VCH: Weinheim, Germany (2018).
  • 104 M. A. Wang,, K. A. Scheidt,. Angew. Chem. Int. Ed.. 2016; 55: 14912
    Google Scholar
  • 105 X.-Y. Chen,, S. Li,, F. Vetica,, M. Kumar,, D. Enders,. iScience. 2018; 2: 1
    Google Scholar
  • 106 A. T. Biju,, N. Kuhl,, F. Glorius,. Acc. Chem. Res.. 2011; 44: 1182
    Google Scholar
  • 107 S. J. Ryan,, L. Candish,, D. W. Lupton,. Chem. Soc. Rev.. 2013; 42: 4906
    Google Scholar
  • 108 Prier, C. K. MacMillan, D. W. C., In Visible Light Photocatalysis in Organic ChemistryStephenson, C. R. J. Yoon, T. P. MacMillan, D. W. C., Eds.; Wiley-VCH: Weinheim, Germany (2018); p 299.
  • 109 D. A. DiRocco,, T. Rovis,. J. Am. Chem. Soc.. 2012; 134: 8094
    Google Scholar
  • 110 R. R. Knowles,, E. N. Jacobsen,. Proc. Natl Acad. Sci. USA. 2010; 107: 20678
    Google Scholar
  • 111 D. Parmar,, E. Sugiono,, S. Raja,, M. Rueping,. Chem. Rev.. 2014; 114: 9047
    Google Scholar
  • 112 T. James,, M. van Gemmeren,, B. List,. Chem. Rev.. 2015; 115: 9388
    Google Scholar
  • 113 M. S. Taylor,, E. N. Jacobsen,. Angew. Chem. Int. Ed.. 2006; 45: 1520
    Google Scholar
  • 114 K. Brak,, E. N. Jacobsen,. Angew. Chem. Int. Ed.. 2013; 52: 534
    Google Scholar
  • 115 C. Brenninger,, J. D. Jolliffe,, T. Bach,. Angew. Chem. Int. Ed.. 2018; 57: 14338
    Google Scholar
  • 116 K. N. Lee,, M. Y. Ngai,. Chem. Commun. (Cambridge). 2017; 53: 13093
    Google Scholar
  • 117 M. H. V. Huynh,, T. J. Meyer,. Chem. Rev.. 2007; 107: 5004
    Google Scholar
  • 118 D. C. Miller,, K. T. Tarantino,, R. R. Knowles,. Top. Curr. Chem.. 2016; 374: 30
    Google Scholar
  • 120 M. Nakajima,, E. Fava,, S. Loeschner,, Z. Jiang,, M. Rueping,. Angew. Chem. Int. Ed.. 2015; 54: 8828
    Google Scholar
  • 121 Thullen, S. M. Ashley, M. A. Rovis, T., In Science of Synthesis: Photocatalysis in Organic SynthesisKönig, B., Ed.; Thieme: Stuttgart (2019); p 219.
  • 122 M. Neumann,, K. Zeitler,. Chem.–Eur. J.. 2013; 19: 6950
    Google Scholar
  • 123 J. Du,, L. R. Espelt,, I. A. Guzei,, T. P. Yoon,. Chem. Sci.. 2011; 2: 2115
    Google Scholar
  • 124 K. T. Tarantino,, P. Liu,, R. R. Knowles,. J. Am. Chem. Soc.. 2013; 135: 10022
    Google Scholar
  • 125 L. J. Rono,, H. G. Yayla,, D. Y. Wang,, M. F. Armstrong,, R. R. Knowles,. J. Am. Chem. Soc.. 2013; 135: 17735
    Google Scholar
  • 126 L. Lin,, X. Bai,, X. Ye,, X. Zhao,, C.-H. Tan,, Z. Jiang,. Angew. Chem. Int. Ed.. 2017; 56: 13842
    Google Scholar
  • 127 T. Maji,, A. Karmakar,, O. Reiser,. J. Org. Chem.. 2011; 76: 736
    Google Scholar
  • 128 M. Hou,, L. Lin,, X. Chai,, X. Zhao,, B. Qiao,, Z. Jiang,. Chem. Sci.. 2019; 10: 6629
    Google Scholar
  • 129 M. A. Emmanuel,, N. R. Greenberg,, D. G. Oblinsky,, T. K. Hyster,. Nature (London). 2016; 540: 414
    Google Scholar
  • 130 B. Qiao,, C. Li,, X. Zhao,, Y. Yin,, Z. Jiang,. Chem. Commun. (Cambridge). 2019; 55: 7534
    Google Scholar
  • 131 T. Shao,, Y. Li,, N. Ma,, C. Li,, G. Chai,, X. Zhao,, B. Qiao,, Z. Jiang,. iScience. 2019; 16: 410
    Google Scholar
  • 133 J. J. Li,. Heterocyclic Chemistry in Drug Discovery. Wiley; Hoboken, NJ 2013
    Google Scholar
  • 134 K. Cao,, S. M. Tan,, R. Lee,, S. Yang,, H. Jia,, X. Zhao,, B. Qiao,, Z. Jiang,. J. Am. Chem. Soc.. 2019; 141: 5437
    Google Scholar
  • 135 Y. Liu,, X. Liu,, J. Li,, X. Zhao,, B. Qiao,, Z. Jiang,. Chem. Sci.. 2018; 9: 8094
    Google Scholar
  • 136 J. Li,, M. Kong,, B. Qiao,, R. Lee,, X. Zhao,, Z. Jiang,. Nat. Commun.. 2018; 9: 2445
    Google Scholar
  • 137 D. Uraguchi,, N. Kinoshita,, T. Kizu,, T. Ooi,. J. Am. Chem. Soc.. 2015; 137: 13768
    Google Scholar
  • 138 H. B. Hepburn,, P. Melchiorre,. Chem. Commun. (Cambridge). 2016; 52: 3520
    Google Scholar
  • 139 Y. Yin,, Y. Dai,, H. Jia,, J. Li,, L. Bu,, B. Qiao,, X. Zhao,, Z. Jiang,. J. Am. Chem. Soc.. 2018; 140: 6083
    Google Scholar
  • 140 R. S. J. Proctor,, R. J. Phipps,. Angew. Chem. Int. Ed.. 2019; 58: 13666
    Google Scholar
  • 141 W.-M. Cheng,, R. Shang,, Y. Fu,. ACS Catal.. 2017; 7: 907
    Google Scholar
  • 142 R. S. J. Proctor,, H. J. Davis,, R. J. Phipps,. Science (Washington, D. C.). 2018; 360: 419
    Google Scholar
  • 143 X. Liu,, Y. Liu,, G. Chai,, B. Qiao,, X. Zhao,, Z. Jiang,. Org. Lett.. 2018; 20: 6298
    Google Scholar
  • 144 D. Zheng,, A. Studer,. Angew. Chem. Int. Ed.. 2019; 58
    Google Scholar
  • 145 Hydrogen-Transfer Reactions Hynes, J. T. Klinman, J. P. Limback, H.-H. Schowen, R. L., Eds.; Wiley-VCH: Weinheim, Germany (2007); Vols. 1–4.
  • 146 Hydrogen Transfer Reactions: Reductions and Beyond Guillena, G. Ramón, D. J., Eds.; Springer: Switzerland (2016).
  • 148 Y. Nakano,, K. F. Biegasiewicz,, T. K. Hyster,. Curr. Opin. Chem. Biol.. 2019; 49: 16
    Google Scholar
  • 150 X.-Z. Fan,, J.-W. Rong,, H.-L. Wu,, Q. Zhou,, H.-P. Deng,, J.-D. Tan,, C.-W. Xue,, L.-Z. Wu,, H.-R. Tao,, J. Wu,. Angew. Chem. Int. Ed.. 2018; 57: 8514
    Google Scholar
  • 151 L. M. Stateman,, K. M. Nakafuku,, D. A. Nagib,. Synthesis. 2018; 50: 1569
    Google Scholar
  • 152 K. A. Margrey,, D. A. Nicewicz,. Acc. Chem. Res.. 2016; 49: 1997
    Google Scholar
  • 153 C. Cassani,, G. Bergonzini,, C.-J. Wallentin,. Org. Lett.. 2014; 16: 4228
    Google Scholar
  • 154 J. D. Griffin,, M. A. Zeller,, D. A. Nicewicz,. J. Am. Chem. Soc.. 2015; 137: 11340
    Google Scholar
  • 155 D. J. Wilger,, N. J. Gesmundo,, D. A. Nicewicz,. Chem. Sci.. 2013; 4: 3160
    Google Scholar
  • 156 D. C. Miller,, G. J. Choi,, H. S. Orbe,, R. R. Knowles,. J. Am. Chem. Soc.. 2015; 137: 13492
    Google Scholar
  • 157 H. Wang,, N. T. Jui,. J. Am. Chem. Soc.. 2018; 140: 163
    Google Scholar
  • 158 A. J. Boyington,, C. P. Seath,, A. M. Zearfoss,, Z. Xu,, N. T. Jui,. J. Am. Chem. Soc.. 2019; 141: 4147
    Google Scholar
  • 159 D. S. Hamilton,, D. A. Nicewicz,. J. Am. Chem. Soc.. 2012; 134: 18577
    Google Scholar
  • 160 D. A. Nicewicz,, D. S. Hamilton,. Synlett. 2014; 25: 1191
    Google Scholar
  • 161 T. M. Nguyen,, N. Manohar,, D. A. Nicewicz,. Angew. Chem. Int. Ed.. 2014; 53: 6198
    Google Scholar
  • 162 T. E. Müller,, K. C. Hultzsch,, M. Yus,, F. Foubelo,, M. Tada,. Chem. Rev.. 2008; 108: 3795
    Google Scholar
  • 163 J. C. K. Chu,, T. Rovis,. Angew. Chem. Int. Ed.. 2018; 57: 62
    Google Scholar
  • 164 N. A. Romero,, K. A. Margrey,, N. E. Tay,, D. A. Nicewicz,. Science (Washington, D. C.). 2015; 349: 1326
    Google Scholar
  • 165 K. A. Margrey,, A. Levens,, D. A. Nicewicz,. Angew. Chem. Int. Ed.. 2017; 56: 15644
    Google Scholar
  • 166 W. Chen,, Z. Huang,, N. E. S. Tay,, B. Giglio,, M. Wang,, H. Wang,, W. Zhanhong,, D. A. Nicewicz,, L. Zibo,. Science (Washington, D. C.). 2019; 364: 1170
    Google Scholar
  • 167 K. Qvortrup,, D. A. Rankic,, D. W. C. MacMillan,. J. Am. Chem. Soc.. 2014; 136: 626
    Google Scholar
  • 168 D. Hager,, D. W. C. MacMillan,. J. Am. Chem. Soc.. 2014; 136: 16986
    Google Scholar
  • 169 M. H. Shaw,, V. W. Shurtleff,, J. A. Terrett,, J. D. Cuthbertson,, D. W. C. MacMillan,. Science (Washington, D. C.). 2016; 352: 1304
    Google Scholar
  • 170 D. R. Heitz,, J. C. Tellis,, G. A. Molander,. J. Am. Chem. Soc.. 2016; 138: 12715
    Google Scholar
  • 171 B. J. Shields,, A. G. Doyle,. J. Am. Chem. Soc.. 2016; 138: 12719
    Google Scholar
  • 172 J. A. Milligan,, J. P. Phelan,, S. O. Badir,, G. A. Molander,. Angew. Chem. Int. Ed.. 2019; 58: 6152
    Google Scholar