Flow Metal-Free Ar-C Bond Formation via Photogenerated Phenyl Cations

Advanced Synthesis and Catalysis

Volumn 358, Issue 7, 2016, Pages 1164-1172

  Bergami, Matteo ^a   Protti, Stefano ^a   Ravelli, Davide ^a   Fagnoni, Maurizio ^a  

^a Department of Chemistry   (Italy)

Author keywords

arylation flow chemistry metal free conditions phenyl cation photochemistry process mass intensity

Indexed keywords

EID: 84961775243     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201600019     Document Type: Article

References (86)

1. Chemical Reactions and Processes Under Flow Conditions, (Eds.:, S. V. Luis, E. Garcia-Verdugo,), RSC Publishing: Cambridge and London, 2009;
2. J. Wegner, S. Ceylan, A. Kirschning, Adv. Synth. Catal. 2012, 354, 17-57;
3. J. C. Pastre, D. L. Browne, S. V. Ley, Chem. Soc. Rev. 2013, 42, 8849-8869;
4. L. Carroccia, B. Musio, L. Degennaro, G. Romanazzi, R. Luisi, J. Flow Chem. 2013, 3, 29-33;
5. Flow Chemistry, (Eds.:, F. Darvas, G. Dorman, V. Hessel,), De Gruyter, 2014;
6. M. Brzozowski, M. O'Brien, S. V. Ley, A. Polyzos, Acc. Chem. Res. 2015, 48, 349-362;
7. F. G. Finelli, L. S. M. Miranda, R. O. M. A. de Souza, Chem. Commun. 2015, 51, 3708-3722;
8. R. Porta, M. Benaglia, A. Puglisi, Org. Process Res. Dev. 2016, 20, 2-25.
9. Microreactors: New Technology for Modern Chemistry, (Eds.:, W. Ehrfeld, V. Hessel, H. Löwe,), Wiley-VCH, Weinheim, 2000;
10. Microreactors in Organic Synthesis and Catalysis, (Ed.:, T. Wirth,), Wiley-VCH, Weinheim, 2008;
11. Flash chemistry: fast organic synthesis in microsystems, (Ed.:, J. Yoshida,), Wiley, Chichester, 2008;
12. A. Cukalovic, J. C. M. R. Monbaliu, C. Stevens, Top. Heterocycl. Chem. 2010, 23, 161-198;
13. J. Fortunak, P. N. Confalone, J. A. Grosso, Curr. Opin. Drug Discovery Dev. 2010, 13, 642-644;
14. A. Kirschning, Beilstein J. Org. Chem. 2009, 5, DOI: 10./bjoc. 5. 15; 3762.
15. R. L. Hartman, K. F. Jensen, Lab Chip 2009, 9, 2495-2507;
16. K. Geyer, T. Gustafsson, P. H. Seeberger, Synlett 2009, 2382-2391;
17. D. T. McQuade, P. H. Seeberger, J. Org. Chem. 2013, 78, 6384-6389.
18. See, for reviews
19. T. Noël, S. L. Buchwald, Chem. Soc. Rev. 2011, 40, 5010-5029;
20. D. Cantillo, C. O. Kappe, ChemCatChem 2014, 6, 3286-3305.
21. P. Li, S. L. Buchwald, Angew. Chem. 2011, 123, 6520-6524;
22. Angew. Chem. Int. Ed. 2011, 50, 6396-6400;
23. B. Egle, J. de M. Muñoz, N. Alonso, W. M. De Borggraeve, A. de La Hoz, A. Díaz-Ortiz, J. Alcázar, J. Flow Chem. 2014, 4, 22-25;
24. V. G. Bhaya, R. A. Joshi, A. A. Kulkarni, J. Flow Chem. 2014, 4, 211-216.
25. S. Liu, T. Fukuyama, M. Sato, I. Ryu, Org. Process Res. Dev. 2004, 8, 477-481;
26. J. P. McMullen, M. T. Stone, S. L. Buchwald, K. F. Jensen, Angew. Chem. 2010, 122, 7230-7234;
27. Angew. Chem. Int. Ed. 2010, 49, 7076-7080;
28. B. Urbán, D. Srankó, G. Sáfrán, L. Ürge, F. Darvas, J. Bakos, R. Skoda-Földes, J. Mol. Catal. A 2014, 395, 364-372;
29. C. Petrucci, M. Cappelletti, O. Piermatti, M. Nocchetti, M. Pica, F. Pizzo, L. Vaccaro, J. Mol. Catal. A 2015, 401, 27-34.
30. R. L. Hartman, J. R. Naber, S. L. Buchwald, K. F. Jensen, Angew. Chem. 2010, 122, 911-915;
31. Angew. Chem. Int. Ed. 2010, 49, 899-903.
32. N. Oger, E. Le Grognec, F.-X. Felpin, J. Org. Chem. 2014, 79, 8255-8262.
33. K. S. Nalivela, M. Tilley, M. A. McGuire, M. G. Organ, Chem. Eur. J. 2014, 20, 6603-6607;
34. N. Chernyak, S. L. Buchwald, J. Am. Chem. Soc. 2012, 134, 12466-12469.
35. T. Nöel, S. Kuhn, A. J. Musacchio, K. F. Jensen, S. L. Buchwald, Angew. Chem. 2011, 123, 6065-6068;
36. Angew. Chem. Int. Ed. 2011, 50, 5943-5946;
37. T. N. Trinh, L. Hizartzidis, A. J. S. Lin, D. G. Harman, A. McCluskey, C. P. Gordon, Org. Biomol. Chem. 2014, 12, 9562-9571.
38. W. Shu, S. L. Buchwald, Angew. Chem. 2012, 124, 5451-5454;
39. Angew. Chem. Int. Ed. 2012, 51, 5355-5358.
40. E. R. Murphy, J. R. Martinelli, N. Zaborenko, S. L. Buchwald, K. F. Jensen, Angew. Chem. 2007, 119, 1764-1767;
41. Angew. Chem. Int. Ed. 2007, 46, 1734-1737;
42. Q. Deng, R. Shen, Z. Zhao, M. Yan, L. Zhang, Chem. Eng. J. 2015, 262, 1168-1174.
43. Z. He, T. F. Jamison, Angew. Chem. 2014, 126, 3421-3425;
44. Angew. Chem. Int. Ed. 2014, 53, 3353-3357;
45. B. K. Singh, C. V. Stevens, D. R. J. Acke, V. S. Parmar, E. V. Van der Eycken, Tetrahedron Lett. 2009, 50, 15-18;
46. F. Ullah, T. Samarakoon, A. Rolfe, R. D. Kurtz, P. R. Hanson, M. G. Organ, Chem. Eur. J. 2010, 16, 10959-10962.
47. X. Wang, G. D. Cuny, T. Noël, Angew. Chem. 2013, 125, 8014-8018;
48. Angew. Chem. Int. Ed. 2013, 52, 7860-7864.
49. R. L. Hartman, J. R. Naber, N. Zaborenko, S. L. Buchwald, K. F. Jensen, Org. Process Res. Dev. 2010, 14, 1347-1357;
50. A. Caron, A. C. Hernandez-Perez, S. K. Collins, Org. Process Res. Dev. 2014, 18, 1571-1574;
51. T. Nöel, J. R. Naber, R. L. Hartman, J. P. McMullen, K. F. Jensen, S. L. Buchwald, Chem. Sci. 2011, 2, 287-290.
52. A. Albini, L. Germani, in Handbook of Synthetic Photochemistry, (Eds.:, A. Albini, M. Fagnoni,), Wiley-VCH Verlag, Weinheim, 2010, pp 1-24.
53. Y. Su, N. J. W. Straathof, V. Hessel, T. Noël, Chem. Eur. J. 2014, 20, 10562-10589.
54. M. Oelgemöller, O. Shvydkiv, Molecules 2011, 16, 7522-7550;
55. rd edn., CRC Press, 2012, pp 49-72;
56. M. Oelgemöller, Chem. Eng. Technol. 2012, 35, 1144-1152;
57. M. Neumann, K. Zeitler, Org. Lett. 2012, 14, 2658-2661.
58. J. P. Knowles, L. D. Elliott, K. I. Booker-Milburn, Beilstein J. Org. Chem. 2012, 8, 2025-2052;
59. Z. J. Garlets, J. D. Nguyen, C. R. J. Stephenson, Isr. J. Chem. 2014, 54, 351-360.
60. J. W. Tucker, Y. Zhang, T. F. Jamison, C. R. J. Stephenson, Angew. Chem. 2012, 124, 4220-4223;
61. Angew. Chem. Int. Ed. 2012, 51, 4144-4147.
62. J. W. Beatty, J. J. Douglas, K. P. Cole, C. R. J. Stephenson, Nat. Commun. 2015, 6, 1038, DOI: 10./ncom ms 8919.
63. N. J. W. Straathof, H. P. L. Gemoets, X. Wang, J. C. Schouten, V. Hessel, T. Noël, ChemSusChem 2014, 7, 1612-1617.
64. M. Baghbanzadeh, T. N. Glasnov, C. O. Kappe, J. Flow Chem. 2013, 3, 109-113.
65. Z. He, M. Bae, J. Wu, T. F. Jamison, Angew. Chem. 2014, 126, 14679-14683;
66. Angew. Chem. Int. Ed. 2014, 53, 14451-14455.
67. K. Ueno, F. Kitagawa, N. Kitamura, Lab Chip 2002, 2, 231-234.
68. D. Cantillo, C. Mateos, J. A. Rincon, O. de Frutos, C. O. Kappe, Chem. Eur. J. 2015, 21, 12894-12898.
69. H. Qrareya, C. Raviola, S. Protti, M. Fagnoni, A. Albini, J. Org. Chem. 2013, 78, 6016-6024;
70. H. Qrareya, S. Protti, M. Fagnoni, J. Org. Chem. 2014, 79, 11527-11533.
71. C. Raviola, D. Ravelli, S. Protti, A. Albini, M. Fagnoni, Synlett 2015, 26, 471-478.
72. S. Protti, M. Fagnoni, A. Albini, Org. Biomol. Chem. 2005, 3, 2868-2871;
73. A. Fraboni, M. Fagnoni, A. Albini, J. Org. Chem. 2003, 68, 4886-4893;
74. S. Protti, M. Fagnoni, A. Albini, J. Org. Chem. 2012, 77, 6473-6479.
75. V. Dichiarante, M. Fagnoni, A. Albini, J. Org. Chem. 2010, 75, 1271-1274.
76. F. Bonassi, D. Ravelli, S. Protti, M. Fagnoni, Adv. Synth. Catal. 2015, 357, 3687-3695.
77. C. Jimenez-Gonzalez, C. S. Ponder, Q. B. Broxterman, J. B. Manley, Org. Process Res. Dev. 2011, 15, 912-917.
78. D. Ravelli, S. Protti, M. Fagnoni, A. Albini, Curr. Org. Chem. 2013, 17, 2366-2373.
79. L. D. Elliott, J. P. Knowles, P. J. Koovits, K. G. Maskill, M. J. Ralph, G. Lejeune, L. J. Edwards, R. I. Robinson, I. R. Clemens, B. Cox, D. D. Pascoe, G. Koch, M. Eberle, M. B. Berry, K. I. Booker-Milburn, Chem. Eur. J. 2014, 20, 15226-15232.
80. B. P. Mason, K. E. Price, J. L. Steinbacher, A. R. Bogdan, D. T. McQuade, Chem. Rev. 2007, 107, 2300-2318;
81. L. Vaccaro, D. Lanari, A. Marrocchi, G. Strappaveccia, Green Chem. 2014, 16, 3680-3704;
82. L. Malet-Sanz, S. L. Flavien, J. Med. Chem. 2012, 55, 4062-4098;
83. B. Gutmann, D. Cantillo, C. O. Kappe, Angew. Chem. 2015, 127, 6788-6832;
84. Angew Chem. Int. Ed. 2015, 54, 6688-6728.
85. C. Pavia, E. Ballerini, L. A. Bivona, F. Giacalone, C. Aprile, L. Vaccaro, M. Gruttadauria, Adv. Synth. Catal. 2013, 355, 2007-2018.
86. E. M. Schuster, P. Wipf, Isr. J. Chem. 2014, 54, 361-370.