Visible Light Mediated Photoredox Catalytic Arylation Reactions

Accounts of Chemical Research

Volumn 49, Issue 8, 2016, Pages 1566-1577

  Ghosh, Indrajit ^a   Marzo, Leyre ^a   Das, Amrita ^a   Shaikh, Rizwan ^a   König, Burkhard ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84982306139     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.6b00229     Document Type: Article

References (59)

1. Ackermann, L. Modern Arylation Methods, 1 st ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2009; p 561.
2. Hari, D. P.; Konig, B. The Photocatalyzed Meerwein Arylation: Classic Reaction of Aryl Diazonium Salts in a New Light Angew. Chem., Int. Ed. 2013, 52, 4734-4743 10.1002/anie.201210276
3. Cano-Yelo, H.; Deronzier, A. Photocatalysis of the Pschorr reaction by Ru(bpy)32+ J. Photochem. 1987, 37, 315-321 10.1016/0047-2670(87)85011-6
4. Cano-Yelo, H.; Deronzier, A. Photocatalysis of the Pschorr reaction by tris-(2,2[prime or minute]-bipyridyl)ruthenium(II) in the phenanthrene series J. Chem. Soc., Perkin Trans. 2 1984, 1093-1098 10.1039/P29840001093
5. Kalyani, D.; McMurtrey, K. B.; Neufeldt, S. R.; Sanford, M. S. Room-Temperature C-H Arylation: Merger of Pd-Catalyzed C-H Functionalization and Visible-Light Photocatalysis J. Am. Chem. Soc. 2011, 133, 18566-18569 10.1021/ja208068w
6. Hari, D. P.; Schroll, P.; König, B. Metal-Free, Visible-Light-Mediated Direct C-H Arylation of Heteroarenes with Aryl Diazonium Salts J. Am. Chem. Soc. 2012, 134, 2958-2961 10.1021/ja212099r
7. Zoller, J.; Fabry, D. C.; Rueping, M. Unexpected Dual Role of Titanium Dioxide in the Visible Light Heterogeneous Catalyzed C-H Arylation of Heteroarenes ACS Catal. 2015, 5, 3900-3904 10.1021/acscatal.5b00668
8. Xue, D.; Jia, Z.-H.; Zhao, C.-J.; Zhang, Y.-Y.; Wang, C.; Xiao, J. Direct Arylation of N-Heteroarenes with Aryldiazonium Salts by Photoredox Catalysis in Water Chem.-Eur. J. 2014, 20, 2960-2965 10.1002/chem.201304120
9. Maity, P.; Kundu, D.; Ranu, B. C. Visible-Light-Photocatalyzed Metal-Free C-H Heteroarylation of Heteroarenes at Room Temperature: A Sustainable Synthesis of Biheteroaryls Eur. J. Org. Chem. 2015, 2015, 1727-1734 10.1002/ejoc.201500006
10. Zhang, J.; Chen, J.; Zhang, X.; Lei, X. Total Syntheses of Menisporphine and Daurioxoisoporphine C Enabled by Photoredox-Catalyzed Direct C-H Arylation of Isoquinoline with Aryldiazonium Salt J. Org. Chem. 2014, 79, 10682-10688 10.1021/jo5020432
11. Hari, D. P.; Hering, T.; König, B. Visible Light Photocatalytic Synthesis of Benzothiophenes Org. Lett. 2012, 14, 5334-5337 10.1021/ol302517n
12. Xiao, T.; Dong, X.; Tang, Y.; Zhou, L. Phenanthrene Synthesis by Eosin Y-Catalyzed, Visible Light- Induced [4 + 2] Benzannulation of Biaryldiazonium Salts with Alkynes Adv. Synth. Catal. 2012, 354, 3195-3199 10.1002/adsc.201200569
13. Schroll, P.; Hari, D. P.; König, B. Photocatalytic Arylation of Alkenes, Alkynes and Enones with Diazonium Salts ChemistryOpen 2012, 1, 130-133 10.1002/open.201200011
14. Jiang, H.; Huang, C.; Guo, J.; Zeng, C.; Zhang, Y.; Yu, S. Direct C-H Functionalization of Enamides and Enecarbamates by Using Visible-Light Photoredox Catalysis Chem.-Eur. J. 2012, 18, 15158-15166 10.1002/chem.201201716
15. Hering, T.; Hari, D. P.; König, B. Visible-Light-Mediated α-Arylation of Enol Acetates Using Aryl Diazonium Salts J. Org. Chem. 2012, 77, 10347-10352 10.1021/jo301984p
16. Hari, D. P.; Hering, T.; König, B. The Photoredox-Catalyzed Meerwein Addition Reaction: Intermolecular Amino-Arylation of Alkenes Angew. Chem., Int. Ed. 2014, 53, 725-728 10.1002/anie.201307051
17. Yao, C.-J.; Sun, Q.; Rastogi, N.; König, B. Intermolecular Formyloxyarylation of Alkenes by Photoredox Meerwein Reaction ACS Catal. 2015, 5, 2935-2938 10.1021/acscatal.5b00314
18. Niu, T. F.; Li, L.; Ni, B. Q.; Bu, M. J.; Cai, C.; Jiang, H. L. Visible-Light-Induced Meerwein Cascade Reactions for the Preparation of -Aryl Esters Eur. J. Org. Chem. 2015, 2015, 5775-5780 10.1002/ejoc.201500659
19. Gu, L.; Jin, C.; Liu, J. Metal-free, visible-light-mediated transformation of aryl diazonium salts and (hetero)arenes: an efficient route to aryl ketones Green Chem. 2015, 17, 3733-3736 10.1039/C5GC00644A
20. Majek, M.; Jacobi von Wangelin, A. Metal-Free Carbonylations by Photoredox Catalysis Angew. Chem., Int. Ed. 2015, 54, 2270-2274 10.1002/anie.201408516
21. Guo, W.; Lu, L.-Q.; Wang, Y.; Wang, Y.-N.; Chen, J.-R.; Xiao, W.-J. Metal-Free, Room-Temperature, Radical Alkoxycarbonylation of Aryldiazonium Salts through Visible-Light Photoredox Catalysis Angew. Chem., Int. Ed. 2015, 54, 2265-2269 10.1002/anie.201408837
22. Sahoo, B.; Hopkinson, M. N.; Glorius, F. Combining Gold and Photoredox Catalysis: Visible Light-Mediated Oxy- and Aminoarylation of Alkenes J. Am. Chem. Soc. 2013, 135, 5505-5508 10.1021/ja400311h
23. Shu, X.-z.; Zhang, M.; He, Y.; Frei, H.; Toste, F. D. Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion J. Am. Chem. Soc. 2014, 136, 5844-5847 10.1021/ja500716j
24. Patil, D. V.; Yun, H.; Shin, S. Catalytic Cross-Coupling of Vinyl Golds with Diazonium Salts under Photoredox and Thermal Conditions Adv. Synth. Catal. 2015, 357, 2622-2628 10.1002/adsc.201500525
25. Tlahuext-Aca, A.; Hopkinson, M. N.; Sahoo, B.; Glorius, F. Dual gold/photoredox-catalyzed C(sp)-H arylation of terminal alkynes with diazonium salts Chem. Sci. 2016, 7, 89-93 10.1039/C5SC02583D
26. He, Y.; Wu, H.; Toste, F. D. A dual catalytic strategy for carbon-phosphorus cross-coupling via gold and photoredox catalysis Chem. Sci. 2015, 6, 1194-1198 10.1039/C4SC03092C
27. Yu, J.; Zhang, L.; Yan, G. Metal-Free, Visible Light-Induced Borylation of Aryldiazonium Salts: A Simple and Green Synthetic Route to Arylboronates Adv. Synth. Catal. 2012, 354, 2625-2628 10.1002/adsc.201200416
28. Liu, Y. X.; Xue, D.; Wang, J. D.; Zhao, C. J.; Zou, Q. Z.; Wang, C.; Xiao, J. L. Room-Temperature Arylation of Arenes and Heteroarenes with Diaryliodonium Salts by Photoredox Catalysis Synlett 2013, 24, 507-513 10.1055/s-0032-1318155
29. Tobisu, M.; Furukawa, T.; Chatani, N. Visible Light-mediated Direct Arylation of Arenes and Heteroarenes Using Diaryliodonium Salts in the Presence and Absence of a Photocatalyst Chem. Lett. 2013, 42, 1203-1205 10.1246/cl.130547
30. Baralle, A.; Fensterbank, L.; Goddard, J. P.; Ollivier, C. Aryl Radical Formation by Copper(I) Photocatalyzed Reduction of Diaryliodonium Salts: NMR Evidence for a Cu-II/Cu-I Mechanism Chem.-Eur. J. 2013, 19, 10809-10813 10.1002/chem.201301449
31. Fumagalli, G.; Boyd, S.; Greaney, M. F. Oxyarylation and Aminoarylation of Styrenes Using Photoredox Catalysis Org. Lett. 2013, 15, 4398-4401 10.1021/ol401940c
32. Neufeldt, S. R.; Sanford, M. S. Combining Transition Metal Catalysis with Radical Chemistry: Dramatic Acceleration of Palladium-Catalyzed C-H Arylation with Diaryliodonium Salts Adv. Synth. Catal. 2012, 354, 3517-3522 10.1002/adsc.201200738
33. Hopkinson, M. N.; Sahoo, B.; Glorius, F. Dual Photoredox and Gold Catalysis: Intermolecular Multicomponent Oxyarylation of Alkenes Adv. Synth. Catal. 2014, 356, 2794-2800 10.1002/adsc.201400580
34. Natarajan, P.; Bala, A.; Mehta, S. K.; Bhasin, K. K. Visible-light photocatalyzed synthesis of 2-aryl N-methylpyrroles, furans and thiophenes utilizing arylsulfonyl chlorides as a coupling partner Tetrahedron 2016, 72, 2521 10.1016/j.tet.2016.03.087
35. Xia, J. D.; Deng, G. B.; Zhou, M. B.; Liu, W.; Xie, P.; Li, J. H. Reusable Visible Light Photoredox Catalysts; Catalyzed Benzylic C(sp(3))-H Functionalization/Carbocyclization Reactions Synlett 2012, 23, 2707-2713 10.1055/s-0032-1317349
36. Deng, G. B.; Wang, Z. Q.; Xia, J. D.; Qian, P. C.; Song, R. J.; Hu, M.; Gong, L. B.; Li, J. H. Tandem Cyclizations of 1,6-Enynes with Arylsulfonyl Chlorides by Using Visible-Light Photoredox Catalysis Angew. Chem., Int. Ed. 2013, 52, 1535-1538 10.1002/anie.201208380
37. Gu, L. J.; Jin, C.; Liu, J. Y.; Ding, H. Y.; Fan, B. M. Transition-metal-free, visible-light induced cyclization of arylsulfonyl chlorides with 2-isocyanobiphenyls to produce phenanthridines Chem. Commun. 2014, 50, 4643-4645 10.1039/c4cc01487a
38. Donck, S.; Baroudi, A.; Fensterbank, L.; Goddard, J. P.; Ollivier, C. Visible-Light Photocatalytic Reduction of Sulfonium Salts as a Source of Aryl Radicals Adv. Synth. Catal. 2013, 355, 1477-1482 10.1002/adsc.201300040
39. Pause, L.; Robert, M.; Saveant, J. M. Can single-electron transfer break an aromatic carbon-heteroatom bond in one step? A novel example of transition between stepwise and concerted mechanisms in the reduction of aromatic iodides J. Am. Chem. Soc. 1999, 121, 7158-7159 10.1021/ja991365q
40. Ghosh, I.; Ghosh, T.; Bardagi, J. I.; Konig, B. Reduction of aryl halides by consecutive visible light-induced electron transfer processes Science 2014, 346, 725-728 10.1126/science.1258232
41. 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 10.1021/cr300503r
42. Pirtsch, M.; Paria, S.; Matsuno, T.; Isobe, H.; Reiser, O. Cu(dap)2Cl As an Efficient Visible-Light-Driven Photoredox Catalyst in Carbon-Carbon Bond-Forming Reactions Chem.-Eur. J. 2012, 18, 7336-7340 10.1002/chem.201200967
43. Rossi, R.; Lessi, M.; Manzini, C.; Marianetti, G.; Bellina, F. Transition Metal-Free Direct C-H (Hetero)arylation of Heteroarenes: A Sustainable Methodology to Access (Hetero)aryl-Substituted Heteroarenes Adv. Synth. Catal. 2015, 357, 3777-3814 10.1002/adsc.201500799
44. Zhou, S. Z.; Doni, E.; Anderson, G. M.; Kane, R. G.; MacDougall, S. W.; Ironmonger, V. M.; Tuttle, T.; Murphy, J. A. Identifying the Roles of Amino Acids, Alcohols and 1,2-Diamines as Mediators in Coupling of Haloarenes to Arenes J. Am. Chem. Soc. 2014, 136, 17818-17826 10.1021/ja5101036
45. Studer, A.; Curran, D. P. Organocatalysis and C-H Activation Meet Radical- and Electron-Transfer Reactions Angew. Chem., Int. Ed. 2011, 50, 5018-5022 10.1002/anie.201101597
46. Cheng, Y. N.; Gu, X. Y.; Li, P. X. Visible-Light Photoredox in Homolytic Aromatic Substitution: Direct Arylation of Arenes with Aryl Halides Org. Lett. 2013, 15, 2664-2667 10.1021/ol400946k
47. Cahard, E.; Schoenebeck, F.; Garnier, J.; Cutulic, S. P. Y.; Zhou, S.; Murphy, J. A. Electron Transfer to Benzenes by Photoactivated Neutral Organic Electron Donor Molecules Angew. Chem., Int. Ed. 2012, 51, 3673-3676 10.1002/anie.201200084
48. Nguyen, J. D.; D'Amato, E. M.; Narayanam, J. M. R.; Stephenson, C. R. J. Engaging unactivated alkyl, alkenyl and aryl iodides in visible-light-mediated free radical reactions Nat. Chem. 2012, 4, 854-859 10.1038/nchem.1452
49. Kim, H.; Lee, C. Visible-Light-Induced Photocatalytic Reductive Transformations of Organohalides Angew. Chem., Int. Ed. 2012, 51, 12303-12306 10.1002/anie.201203599
50. Meyer, A. U.; Slanina, T.; Yao, C.-J.; Koenig, B. Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis ACS Catal. 2016, 6, 369-375 10.1021/acscatal.5b02410
51. Senaweera, S.; Weaver, J. D. Dual C-F, C-H Functionalization via Photocatalysis: Access to Multifluorinated Biaryls J. Am. Chem. Soc. 2016, 138, 2520-2523 10.1021/jacs.5b13450
52. Discekici, E. H.; Treat, N. J.; Poelma, S. O.; Mattson, K. M.; Hudson, Z. M.; Luo, Y. D.; Hawker, C. J.; de Alaniz, J. R. A highly reducing metal-free photoredox catalyst: design and application in radical dehalogenations Chem. Commun. 2015, 51, 11705-11708 10.1039/C5CC04677G
53. Ghosh, I.; König, B. Chromoselective Photocatalysis: Controlled bond activation via light-color regulation of redox potentials Angew. Chem., Int. Ed. 2016, 55, 7676-7679 10.1002/anie.201602349
54. Gosztola, D.; Niemczyk, M. P.; Svec, W.; Lukas, A. S.; Wasielewski, M. R. Excited doublet states of electrochemically generated aromatic imide and diimide radical anions J. Phys. Chem. A 2000, 104, 6545-6551 10.1021/jp000706f
55. Zeng, L.; Liu, T.; He, C.; Shi, D.; Zhang, F.; Duan, C. Organized Aggregation Makes Insoluble Perylene Diimide Efficient for the Reduction of Aryl Halides via Consecutive Visible Light-Induced Electron-Transfer Processes J. Am. Chem. Soc. 2016, 138, 3958-3961 10.1021/jacs.5b12931
56. Majek, M.; Faltermeier, U.; Dick, B.; Perez-Ruiz, R.; Jacobi von Wangelin, A. Application of Visible-to-UV Photon Upconversion to Photoredox Catalysis: The Activation of Aryl Bromides Chem.-Eur. J. 2015, 21, 15496-15501 10.1002/chem.201502698
57. Costentin, C.; Robert, M.; Saveant, J. M. Fragmentation of aryl halide pi anion radicals. Bending of the cleaving bond and activation vs driving force relationships J. Am. Chem. Soc. 2004, 126, 16051-16057 10.1021/ja045989u
58. Majek, M.; Filace, F.; Jacobi von Wangelin, A. Visible Light Driven Hydro-/Deuterodefunctionalization of Anilines Chem.-Eur. J. 2015, 21, 4518-4522 10.1002/chem.201406461
59. van de Linde, S.; Krstic, I.; Prisner, T.; Doose, S.; Heilemann, M.; Sauer, M. Photoinduced formation of reversible dye radicals and their impact on super-resolution imaging Photochem. Photobiol. Sci. 2011, 10, 499-506 10.1039/C0PP00317D