Preparative Scale Demonstration and Mechanistic Investigation of a Visible Light-Mediated Radical Smiles Rearrangement

Organic Process Research and Development

Volumn 20, Issue 7, 2016, Pages 1148-1155

  Douglas, James J ^a,b   Sevrin, Martin J ^a   Cole, Kevin P ^b   Stephenson, Corey R J ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY;

CONTINUOUS FLOWS; PHARMACEUTICAL DEVELOPMENT; RADICAL CHAIN; SCALE-UP; SMILES REARRANGEMENT; THERMAL ACTIVATION; THERMAL INITIATIONS; VISIBLE LIGHT;

LIGHT;

EID: 84978473823     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/acs.oprd.6b00126     Document Type: Article

References (52)

1. Tucker, J. W.; Stephenson, C. R. J. J. Org. Chem. 2012, 77, 1617-1622 10.1021/jo202538x
2. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322-5363 10.1021/cr300503r
3. Nicewicz, D. A.; Nguyen, T. M. ACS Catal. 2014, 4, 355-360 10.1021/cs400956a
4. Douglas, J. J.; Nguyen, J. D.; Cole, K. P.; Stephenson, C. R. J. Aldrichimica Acta 2014, 47, 16-27
5. Douglas, J. J.; Sevrin, M. J.; Stephenson, C. R. J. Org. Process Res. Dev. 2016, 10.1021/acs.oprd.6b00125.
6. Hari, D. P.; Hering, T.; König, B. Org. Lett. 2012, 14, 5334-5337 10.1021/ol302517n
7. Douglas, J. J.; Cole, K. P.; Stephenson, C. R. J. J. Org. Chem. 2014, 79, 11631-11643 10.1021/jo502288q
8. Chu, L.; Lipshultz, J. M.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2015, 54, 7929-7933 10.1002/anie.201501908
9. Le, C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 11938-11941 10.1021/jacs.5b08304
10. Douglas, J. J.; Albright, H.; Sevrin, M. J.; Cole, K. P.; Stephenson, C. R. J. Angew. Chem., Int. Ed. 2015, 54, 14898-14902 10.1002/anie.201507369
11. Halperin, S. D.; Kwon, D.; Holmes, M.; Regalado, E. L.; Campeau, L.-C.; DiRocco, D. A.; Britton, R. Org. Lett. 2015, 17, 5200-5203 10.1021/acs.orglett.5b02532
12. Yayla, H. G.; Peng, F.; Mangion, I. K.; McLaughlin, M.; Campeau, L.-C.; Davies, I. W.; DiRocco, D. A.; Knowles, R. R. Chem. Sci. 2016, 7, 2066-2073 10.1039/C5SC03350K
13. Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224-228 10.1038/nature10647
14. DiRocco, D. A.; Dykstra, K.; Krska, S.; Vachal, P.; Conway, D. V.; Tudge, M. Angew. Chem., Int. Ed. 2014, 53, 4802-4806 10.1002/anie.201402023
15. Romero, N. A.; Margrey, K. A.; Tay, N. E.; Nicewicz, D. A. Science 2015, 349, 1326-1330 10.1126/science.aac9895
16. Levy, A. A.; Rains, H. C.; Smiles, S. J. Chem. Soc. 1931, 0, 3264-3269 10.1039/JR9310003264
17. Matsui, K.; Maeno, N.; Suzuki, S.; Shizuka, H.; Morita, T. Tetrahedron Lett. 1970, 11, 1467-1469 10.1016/S0040-4039(01)97997-3
18. Wang, Z. In Comprehensive Organic Name Reactions and Reagents; John Wiley & Sons, Inc., 2010. For the radical Smiles rearrangement see:.
19. Loven, R.; Speckamp, W. N. Tetrahedron Lett. 1972, 13, 1567-1570 10.1016/S0040-4039(01)84687-6
20. Motherwell, W. B.; Pennell, A. M. K. J. Chem. Soc., Chem. Commun. 1991, 877-879 10.1039/c39910000877
21. Studer, A.; Bossart, M. Tetrahedron 2001, 57, 9649-9667 10.1016/S0040-4020(01)00990-5
22. Chen, Z.-M.; Zhang, X.-M.; Tu, Y.-Q. Chem. Soc. Rev. 2015, 44, 5220-5245 10.1039/C4CS00467A
23. Tada, M.; Shijima, H.; Nakamura, M. Org. Biomol. Chem. 2003, 1, 2499-2505 10.1039/b303728b
24. Kong, W.; Casimiro, M.; Merino, E.; Nevado, C. J. Am. Chem. Soc. 2013, 135, 14480-14483 10.1021/ja403954g
25. Studer, A.; Bossart, M. Chem. Commun. 1998, 2127-2128 10.1039/a806718j
26. Bossart, M.; Fässler, R.; Schoenberger, J.; Studer, A. Eur. J. Org. Chem. 2002, 2002, 2742-2757 10.1002/1099-0690(200208)2002:16<2742::AID-EJOC2742>3.0.CO;2-R
27. DeBaillie, A. C.; Jones, C. D.; Magnus, N. A.; Mateos, C.; Torrado, A.; Wepsiec, J. P.; Tokala, R.; Raje, P. Org. Process Res. Dev. 2015, 19, 1568 10.1021/op5000094
28. Van Bergen, T. J.; Hedstrand, D. M.; Kruizinga, W. H.; Kellogg, R. M. J. Org. Chem. 1979, 44, 4953-4962 10.1021/jo00394a044
29. Hironaka, K.; Fukuzumi, S.; Tanaka, T. J. Chem. Soc., Perkin Trans. 2 1984, 1705-1709 10.1039/p29840001705
30. Kern, J.-M.; Sauvage, J.-P. J. Chem. Soc., Chem. Commun. 1987, 546-548 10.1039/C39870000546
31. Fukuzumi, S.; Mochizuki, S.; Tanaka, T. J. Phys. Chem. 1990, 94, 722-726 10.1021/j100365a039
32. Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. J. Am. Chem. Soc. 2009, 131, 8756-8757 10.1021/ja9033582
33. Nguyen, J. D.; D'Amato, E. M.; Narayanam, J. M. R.; Stephenson, C. R. J. Nat. Chem. 2012, 4, 854-859 10.1038/nchem.1452
34. Ismaili, H.; Pitre, S. P.; Scaiano, J. C. Catal. Sci. Technol. 2013, 3, 935-937 10.1039/c3cy20759e
35. McTiernan, C. D.; Pitre, S. P.; Scaiano, J. C. ACS Catal. 2014, 4, 4034-4039 10.1021/cs501030f
36. Pitre, S. P.; McTiernan, C. D.; Ismaili, H.; Scaiano, J. C. ACS Catal. 2014, 4, 2530-2535 10.1021/cs5005823
37. Kärkäs, M. D.; Matsuura, B. S.; Stephenson, C. R. J. Science 2015, 349, 1285-1286 10.1126/science.aad0193
38. Cismesia, M. A.; Yoon, T. P. Chem. Sci. 2015, 6, 5426-5434 10.1039/C5SC02185E
39. Pitre, S. P.; McTiernan, C. D.; Vine, W.; DiPucchio, R.; Grenier, M.; Scaiano, J. C. Sci. Rep. 2015, 5, 16397 10.1038/srep16397
40. Beatty, J. W.; Douglas, J. J.; Cole, K. P.; Stephenson, C. R. J. Nat. Commun. 2015, 6, 7919 10.1038/ncomms8919
41. Fouassier, J. P.; Burr, D. Macromolecules 1990, 23, 3615-3619 10.1021/ma00217a013
42. Reductions of carbon centered radicals are typically observed when the resulting anion can be delocalized into an adjacent pi system, for example see: Jovanovic, S. V.; Steenken, S.; Simic, M. G. J. Phys. Chem. 1990, 94, 3583-3588 Such a reduction would also represent a chain termination event in competition with other intermolecular processes, such as C-H abstraction leading to 16. We kindly thank a reviewer for expanding upon this possibility. 10.1021/j100372a041
43. Chatgilialoglu, C.; Griller, D.; Rossini, S. J. Org. Chem. 1989, 54, 2734-2737 10.1021/jo00272a052
44. Qrareya, H.; Protti, S.; Fagnoni, M. J. Org. Chem. 2014, 79, 11527-11533 See also ref 11 10.1021/jo502172c
45. Beckwith, A. L. J.; Norman, R. O. C. J. Chem. Soc. B 1969, 400 10.1039/j29690000400
46. Surdhar, P. S.; Mezyk, S. P.; Armstrong, D. A. J. Phys. Chem. 1989, 93, 3360-3363 10.1021/j100345a094
47. Rosso, J. A.; Bertolotti, S. G.; Braun, A. M.; Mártire, D. O.; Gonzalez, M. C. J. Phys. Org. Chem. 2001, 14, 300-309 10.1002/poc.365
48. Juris, A.; Balzani, V.; Barigelletti, F.; Campagna, S.; Belser, P.; von Zelewsky, A. Coord. Chem. Rev. 1988, 84, 85-277 10.1016/0010-8545(88)80032-8
49. DeRosa, M. C.; Crutchley, R. J. Coord. Chem. Rev. 2002, 233-234, 351-371 10.1016/S0010-8545(02)00034-6
50. We do not believe that a high photon flux is required as reactions could be initiated with the ambient light of the laboratory if the level of oxygen was sufficiently low. The sulfonate 1 has no significant absorption above 350 nm however the bond dissociation enthalpy of 1 is likely <69 kcal/mol. Pickard, J. M.; Rodgers, A. S. Int. J. Chem. Kinet. 1977, 9, 759-767 10.1002/kin.550090507
51. For an excellent analysis on catalysis in radical reactions see Studer, A.; Curran, D. P. Angew. Chem., Int. Ed. 2016, 1, 58-102 For the use of quantum yields as an indication of radical propagation see refs 6d and 6f 10.1002/anie.201505090
52. Joachim, J. J.; Masashi, N.; Yuji, H.; Masaki, F.; Satoru, N. US Patent US2011/15431A1, 2011.