Amine functionalization via oxidative photoredox catalysis: Methodology development and complex molecule synthesis

Accounts of Chemical Research

Volumn 48, Issue 5, 2015, Pages 1474-1484

  Beatty, Joel W ^a   Stephenson, Corey R J ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; SYNTHESIS;

AMINES; CATALYSIS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHOTOCHEMICAL PROCESSES;

EID: 84929579479     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.5b00068     Document Type: Article

References (67)

1. Kärkäs, M. D.; Verho, O.; Johnston, E. V.; Åkermark, B. Artificial Photosynthesis: Molecular Systems for Catalytic Water Oxidation Chem. Rev. 2014, 114, 11863-12001
2. Morris, A. J.; Meyer, G. J.; Fujita, E. Molecular Approaches to the Photocatalytic Reduction of Carbon Dioxide for Solar Fuels Acc. Chem. Res. 2009, 42, 1983-1994
3. Juris, A.; Balzani, V.; Barigelletti, F.; Campagna, S.; Belser, P.; von Zelewski, A. Ru(II) Poylpyridine Complexes: Photophysics, Photochemistry, Electrochemistry, and Chemiluminescence Coord. Chem. Rev. 1988, 84, 85-277
4. Nicewicz, D. A.; MacMillan, D. W. C. Merging Photoredox Catalysis with Organocatalysis: The Direct Asymmetric Alkylation of Aldehydes Science 2008, 322, 77-80
5. Ischay, M. A.; Anzovino, M. E.; Du, J.; Yoon, T. P. Efficient Visible Light Photocatalysis of [2 + 2] Enone Cycloadditions J. Am. Chem. Soc. 2008, 130, 12886-12887
6. Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. Electron-Transfer Photoredox Catalysis: Development of a Tin-Free Reductive Dehalogenation Reaction J. Am. Chem. Soc. 2009, 131, 8756-8757
7. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis Chem. Rev. 2013, 113, 5322-5363
8. Wallentin, C. J.; Nguyen, J. D.; Stephenson, C. R. J. Radical Carbon-Carbon Bond Formations Enabled by Visible Light Active Photocatalysts Chimia 2012, 66, 394-398
9. Xuan, J.; Xiao, W. J. Visible-Light Photoredox Catalysis Angew. Chem., Int. Ed. 2012, 51, 6828-6838
10. Shi, L.; Xia, W. Photoredox Functionalization of C-H Bonds Adjacent to a Nitrogen Atom Chem. Soc. Rev. 2012, 41, 7687-7697
11. Lindsay Smith, J. R.; Masheder, D. Amine Oxidation. Part IX. The Electrochemical Oxidation of Some Tertiary Amines: The Effect of Structure on Reactivity J. Chem. Soc., Perkin Trans. 2 1976, 47-51
12. Hu, J.; Wang, J.; Nguyen, T. H.; Zheng, N. The Chemistry of Amine Radical Cations Produced by Visible Light Photoredox Catalysis Beilstein J. Org. Chem. 2013, 9, 1977-2001
13. DeLaive, P. J.; Sullivan, B. P.; Meyer, T. J.; Whitten, D. G. Applications of Light-Induced Electron-Transfer Reactions. Coupling of Hydrogen Generation with Photoreduction of Ruthenium (II) Complexes by Triethylamine J. Am. Chem. Soc. 1979, 101, 4007-4008
14. Bock, C. R.; Connor, J. A.; Gutierrez, A. R.; Meyer, T. J.; Whitten, D. G.; Sullivan, B. P.; Nagle, J. K. Estimation of Excited-State Redox Potentials by Electron-Transfer Quenching. Application of Electron-Transfer Theory to Excited-State Redox Processes J. Am. Chem. Soc. 1979, 101, 4815-4824
15. For the oxidation potential of Et3N vs AgNO3 in MeCN, converted to SCE in Scheme 1, see: Newman, J. D. S.; Blanchard, G. J. Formation of Gold Nanoparticles Using Amine Reducing Agents Langmuir 2006, 22, 5882-5887
16. Estimation of the p K a of the α-C-H bond of the triethylamine radical cation was performed according to eq 19 found in Nicholas, M. de P.; Arnold, D. R. Thermochemical Parameters for Organic Radicals and Radical Ions. Part 1. The Estimation of the p K a of Radical Cations Based on Thermochemical Calculations Can. J. Chem. 1982, 60, 2165-2179
17. Estimation of the α-C-H BDE of the triethylamine radical cation was performed with BDE values from ref 29 according to Wayner, D. D. M.; Dannenberg, J. J.; Griller, D. Oxidation Potentials of α-Amino Radicals: Bond Dissociation Energies for Related Radical Cations Chem. Phys. Lett. 1986, 131, 189-191
18. Lewis, F. D.; Ho, T.-I. On the Selectivity of Tertiary Amine Oxidations J. Am. Chem. Soc. 1980, 102, 1751-1752
19. Lewis, F. D.; Ho, T.-I.; Simpson, J. T. Photochemical Addition of Tertiary Amines to Stillbene. Stereoelectronic Control of Tertiary Amine Oxidation J. Org. Chem. 1981, 46, 1077-1082
20. Zhang, X.; Yeh, S.-R.; Hong, S.; Freccero, M.; Albini, A.; Falvey, D. E.; Mariano, P. S. Dynamics of α-CH Deprotonation and α-Desilylation Reactions of Tertiary Amine Cation Radicals J. Am. Chem. Soc. 1994, 116, 4211-4220
21. Anne, A.; Hapoit, P.; Moiroux, J.; Neta, P.; Saveant, J.-M. Dynamics of Proton Transfer from Cation Radicals. Kinetic and Thermodynamic Acidities of Cation Radicals of NADH Analogues J. Am. Chem. Soc. 1992, 114, 4694-4701
22. Yoon, U. C.; Su, Z.; Mariano, P. S. The Dynamics and Photochemical Consequences of Aminium Radical Reactions. In CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed.; Horspool, W.; Lenci, F., Eds.; CRC Press; Boca Raton, FL, 2004; Vol. 2, pp 101-1-101-20.
23. Schmittel, M.; Burghart, A. Understanding Reactivity Patterns of Radical Cations Angew. Chem., Int. Ed. Engl. 1997, 36, 2550-2589
24. Carroll, A. R.; Hyde, E.; Smith, J.; Quinn, R. J.; Guymer, G.; Forster, P. I. Actinophyllic Acid, a Potent Indole Alkaloid Inhibitor of the Coupled Enzyme Assay Carboxypeptidase U/Hippurcase from the Leaves of Alstonia actinophylla (Apocynaceae) J. Org. Chem. 2005, 70, 1096-1099
25. Bruncko, M.; Crich, D.; Samy, R. Chemistry of Cyclic Tautomers of Tryptophan: Formation of a Quaternary Center at C3a and Total Synthesis of the Marine Alkaloid (+)- ent -Debromoflustramine B J. Org. Chem. 1994, 59, 5543-5549
26. Depew, K. M.; Marsden, S. P.; Zatorska, D.; Zatorski, A.; Bornmann, W. G.; Danishefsky, S. J. Total Synthesis of 5- N -Acetylardeemin and Amauromine: Practical Routes to Potential MDR Reversal Agents J. Am. Chem. Soc. 1999, 121, 11953-11963
27. Kim, J.; Ashenhurst, J. A.; Movassaghi, M. Total Synthesis of (+)-11,11-Dideoxyverticillin A Science 2009, 324, 238-241
28. Van Bergen, T. J.; Hedstrand, D. M.; Kruizinga, W. H.; Kellog, R. M. Hydride Transfer from 1,4-Dihydropyridines to sp3-Hybridized Carbon in Sulfonium Salts and Activated Halides. Studies with NAD(P)H models J. Org. Chem. 1979, 44, 4953-4962
29. Hironaka, K.; Fukuzumi, S.; Tanaka, T. Tris(bipyridyl)Ruthenium(II)-Photosensitized Reaction of 1-Benzyl-1,4-Dihydronicotinamide with Benzyl bromide J. Chem. Soc., Perkin Trans. 2 1984, 1705-1709
30. Fukuzumi, S.; Mochizuki, S.; Tanaka, T. Photocatalytic Reduction of Phenacyl Halides by 9,10-Dihydro-10-Methylacridine. Control Between the Reductive and Oxidative Quenching Pathways of Tris(bipyridine)Ruthenium Complex Utilizing an Acid Catalysis J. Phys. Chem. 1990, 94, 722-726
31. Tucker, J. W.; Narayanam, J. M. R.; Krabbe, S. W.; Stephenson, C. R. J. Electron Transfer Photoredox Catalysis: Intramolecular Radical Addition to Indoles and Pyrroles Org. Lett. 2010, 12, 368-371
32. Magolan, J.; Kerr, M. A. Expanding the Scope of Mn(OAc)3-Mediated Cyclizations: Synthesis of the Tetracyclic Core of Tronocarpine Org. Lett. 2006, 8, 4561-4564
33. Furst, L.; Matsuura, B. S.; Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. Visible Light-Mediated Intermolecular C-H Functionalization of Electron-Rich Heterocycles with Malonates Org. Lett. 2010, 12, 3104-3107
34. Condie, A. G.; González-Gómez, J. C.; Stephenson, C. R. J. Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C-H Functionalization J. Am. Chem. Soc. 2010, 132, 1464-1465
35. Murahashi, S. I.; Zhang, D. Ruthenium Catalyzed Biomimetic Oxidation in Organic Synthesis Inspired by Cytochrome P-450 Chem. Soc. Rev. 2008, 37, 1490-1501
36. Li, C. J. Cross-Dehydrogenative Coupling (CDC): Exploring C-C Bond Formations Beyond Functional Group Transformations Acc. Chem. Res. 2009, 42, 335-344
37. Zhu, S.; Das, A.; Bui, L.; Zhou, H.; Curran, D. P.; Rueping, M. Oxygen Switch in Visible-Light Photoredox Catalysis: Radical Additions and Cyclizations and Unexpected C-C-Bond Cleavage Reactions J. Am. Chem. Soc. 2013, 135, 1823-1829
38. Slinker, J. D.; Gorodetsky, A. A.; Lowry, M. S.; Wang, J.; Parker, S.; Rohl, R.; Bernhard, S.; Malliaras, G. G. Efficient Yellow Electroluminescence from a Single Layer of a Cyclometallated Iridium Complex J. Am. Chem. Soc. 2004, 126, 2763-2767
39. Espelt, L. R.; Wiensch, E. M.; Yoon, T. P. Brønsted Acid Cocatalysts in Photocatalytic Radical Addition of α-Amino C-H Bonds across Michael Acceptors J. Org. Chem. 2013, 78, 4107-4114
40. Mitkina, T.; Stanglmair, C.; Setzer, W.; Gruber, M.; Kisch, H.; König, B. Visible Light Mediated Homo- and Heterocoupling of Benzyl Alcohols and Benzyl Amines on Polycrystaline Cadmium Sulfide Org. Biomol. Chem. 2012, 10, 3556-3561
41. McMillen, D. F.; Golden, D. M. Hydrocarbon Bond Dissociation Energies Annu. Rev. Phys. Chem. 1982, 33, 493-532
42. Dombrowski, G. W.; Dinnocenzo, J. P.; Farid, S.; Goodman, J. L.; Gould, I. R. α-C-H Bond Dissociation Energies of Some Tertiary Amines J. Org. Chem. 1999, 64, 427-431
43. Wallentin, C. J.; Nguyen, J. D.; Finkbeiner, P.; Stephenson, C. R. J. Visible Light-Mediated Atom Transfer Radical Addition via Oxidative and Reductive Quenching of Photocatalysts J. Am. Chem. Soc. 2012, 134, 8875-8884
44. Tucker, J. W.; Zhang, Y.; Jamison, T. F.; Stephenson, C. R. J. Visible-Light Photoredox Catalysis in Flow Angew. Chem., Int. Ed. 2012, 51, 4144-4147
45. Bergonzini, G.; Schindler, C. S.; Wallentin, C. J.; Jacobsen, E. N.; Stephenson, C. R. J. Photoredox Activation and Anion Binding Catalysis in the Dual Catalytic Enantioselective Synthesis of β-Amino Esters Chem. Sci. 2014, 5, 112-116
46. Pan, Y.; Wang, S.; Kee, C. W.; Dubuisson, E.; Yang, Y.; Loh, K. P.; Tan, C. H. Graphene Oxide and Rose Bengal: Oxidative C-H Functionalization of Tertiary Amines Using Visible Light Green Chem. 2011, 13, 3341-3344
47. Rueping, M.; Vila, C.; Koenigs, R. M.; Poscharny, K.; Fabry, D. C. Dual Catalysis: Combining Photoredox and Lewis Base Catalysis for Direct Mannich Reactions Chem. Commun. 2011, 47, 2360-2362
48. Rueping, M.; Zhu, S.; Koenigs, R. M. Photoredox Catalyzed C-P Bond Forming Reactions-Visible Light Mediated Oxidative Phosphonylations of Amines Chem. Commun. 2011, 47, 8679-8681
49. Zhao, G.; Yang, C.; Guo, L.; Sun, H.; Chen, C.; Xia, W. Visible Light-Induced Oxidative Coupling Reaction: Easy Access to Mannich-Type Products Chem. Commun. 2012, 48, 2337-2339
50. Fu, W.; Guo, W.; Zou, G.; Xu, C. Selective Trifluoromethylation and Alkynylation of Tetrahydroisoquinolines Using Visible Light Irradiation by Rose Bengal J. Fluorine Chem. 2012, 140, 88-94
51. Xuan, J.; Feng, Z. J.; Duan, S. W.; Xiao, W. J. Room Temperature Synthesis of Isoquino[2,1- a ][3,1]oxazine and Isoquino[2,1- a ]pyrimidine Derivatives via Visible Light Photoredox Catalysis RSC Adv. 2012, 2, 4065-4068
52. Mathis, C. L.; Gist, B. M.; Frederickson, C. K.; Midkiff, K. M.; Marvin, C. C. Visible Light Photooxidative Cyclization of Amino Alcohols to 1,3-Oxazines Tetrahedron Lett. 2013, 54, 2101-2104
53. Feng, Z. J.; Xuan, J.; Xia, X. D.; Ding, W.; Guo, W.; Chen, J. R.; Zou, Y. Q.; Lu, L. Q.; Xiao, W. J. Direct sp3 C-H Acroleination of N -aryl-Tetrahydroisoquinolines by Merging Photoredox Catalysis with Nucleophilic Catalysis Org. Biomol. Chem. 2014, 12, 2037-2040
54. Xiao, T.; Li, L.; Lin, G.; Mao, Z.; Zhou, L. Metal-Free Visible-Light Induced Cross-Dehydrogenative Couping of Tertiary Amines with Diazo Compounds Org. Lett. 2014, 16, 4232-4235
55. Zou, Y. Q.; Lu, L. Q.; Fu, L.; Chang, N. J.; Rong, J.; Chen, J. R.; Xiao, W. J. Visible-Light-Induced Oxidation/[3 + 2] Cycloaddition/Oxidative Aromatization Sequence: A Photocatalytic Strategy to Construct Pyrrolo[2,1- a ]isoquinolines Angew. Chem., Int. Ed. 2011, 50, 7171-7175
56. DiRocco, D. A.; Rovis, T. Catalytic Asymmetric α-Acylation of Tertiary Amines Mediated by a Dual Catalysis Mode: N -Heterocyclic Carbene and Photoredox Catalysis J. Am. Chem. Soc. 2012, 134, 8094-8097
57. Ishikawa, H.; Colby, D. A.; Boger, D. L. Direct Coupling of Catharanthine and Vindoline to Provide Vinblastine: Total Synthesis of (+)- and ent -(-)-Vinblastine J. Am. Chem. Soc. 2008, 130, 420-421
58. Ishikawa, H.; Colby, D. A.; Seto, S.; Va, P.; Tam, A.; Kakei, H.; Rayl, T. J.; Hwang, I.; Boger, D. A. Total Synthesis of Vinblastine, Vincristine, Related Natural Products, and Key Structural Analogues J. Am. Chem. Soc. 2009, 131, 4904-4916
59. Gotoh, H.; Sears, J. E.; Eschenmoser, A.; Boger, D. L. New Insights into the Mechanism and an Expanded Scope of the Fe(III)-Mediated Vinblastine Coupling Reaction J. Am. Chem. Soc. 2012, 134, 13240-13243
60. Maity, S.; Zhu, M.; Shinabery, R. S.; Zheng, N. Intermolecular [3 + 2] Cycloaddition of Cyclopropylamines with Olefins by Visible-Light Photocatalysis Angew. Chem., Int. Ed. 2012, 51, 222-226
61. Cai, S.; Zhao, X.; Wang, X.; Liu, Q.; Li, Z.; Wang, D. Z. Visible-Light-Promoted C-C Bond Cleavage: Photocatalytic Generation of Iminium Ions and Amino Radicals Angew. Chem., Int. Ed. 2012, 51, 8050-8053
62. Sundberg, R. J.; Desos, P.; Gadamasetti, K. G.; Sabat, M. Photoactive C16-C21 Fragmentation of Catharanthine Tetrahedron Lett. 1991, 32, 3035-3038
63. Cocquet, G.; Rool, P.; Ferroud, C. A Catalytic Versus Stoichiometric Electron Transfer Promoted Selective C16-C21 Bond Cleavage of Catharanthine Tetrahedron Lett. 2001, 42, 839-841
64. Beatty, J. W.; Stephenson, C. R. J. Synthesis of (-)-Pseudotabersonine, (-)-Pseudovincadifformine, and (+)-Coronaridine Enabled by Photoredox Catalysis in Flow J. Am. Chem. Soc. 2014, 136, 10270-10273
65. Douglas, J. J.; Cole, K. P.; Stephenson, C. R. J. Photoredox Catalysis in a Complex Pharmaceutical Setting: Toward the Preparation of JAK2 Inhibitor LY2784544 J. Org. Chem. 2014, 79, 11631-11643
66. Mitchell, D.; Cole, K. P.; Pollock, P. M.; Coppert, D. M.; Burkholder, T. P.; Clayton, J. R. Development and a Practical Synthesis of the JAK2 inhibitor LY2784544 Org. Process Res. Dev. 2012, 16, 70-81
67. Dai, C.; Meschini, F.; Narayanam, J. M. R.; Stephenson, C. R. J. Friedel-Crafts Amidoalkylation via Thermolysis and Oxidative Photocatalysis J. Org. Chem. 2012, 77, 4425-4431