Photocatalytic initiation of thiol-ene reactions: Synthesis of thiomorpholin-3-ones

Tetrahedron

Volumn 70, Issue 27-28, 2014, Pages 4264-4269

  Keylor, Mitchell H ^a   Park, James E ^b   Wallentin, Carl Johan ^b   Stephenson, Corey R J ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b Boston University   (United States)

Author keywords

Click reaction; Hydrothiolation; Photoredox catalysis; Thiol ene; Thiomorpholinone

Indexed keywords

ALKENE; LEWIS ACID; SOLVENT; THIOL; THIOMORPHOLIN 3 ONE DERIVATIVE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; HYDROTHIOLATION; LIGHT; ONE POT SYNTHESIS; PHOTOCATALYSIS; PRIORITY JOURNAL;

EID: 84901347271     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.03.041     Document Type: Article

References (49)

1. A. Gress, A. Volkel, and H. Schlaad Macromolecules 40 2007 7928 7933
2. T. Posner Ber. Dtsch. Chem. Ges. 38 1905 646 657
3. C.E. Hoyle, A.B. Lowe, and C.N. Bowman Chem. Soc. Rev. 39 2010 1355 1387
4. C.E. Hoyle, and C.N. Bowman Angew. Chem., Int. Ed. 49 2010 1540 1573
5. C.E. Hoyle, T.Y. Lee, and T. Roper J. Polym. Sci., Part A: Polym. Chem. 42 2004 5301 5338
6. A.B. Lowe Polym. Chem. 1 2010 17 36
7. M.J. Kade, D.J. Burke, and C.J. Hawker J. Polym. Sci., Part A: Polym. Chem. 48 2010 743 750
8. A.B. Lowe, and A.M. Harvison Aust. J. Chem. 63 2010 1251 1266
9. A.K. Tucker-Schwartz, R.A. Farrell, and R.L. Garrell J. Am. Chem. Soc. 133 2011 11026 11029
10. H. Mizuno, and J.M. Buriak J. Am. Chem. Soc. 130 2008 17656 17657
11. C. Rissing, and D.Y. Son Organometallics 28 2009 3167 3172
12. K. Lorenz, H. Frey, B. Stuhn, and R. Mulhaupt Macromolecules 30 1997 6860 6868
13. B.M. Rosen, G. Lligadas, C. Hahn, and V. Percec J. Polym. Sci., Part A: Polym. Chem. 47 2009 3940 3948
14. K.L. Killops, L.M. Campos, and C.J. Hawker J. Am. Chem. Soc. 130 2008 5062 5064
15. M. Fiore, A. Marra, and A. Dondoni J. Org. Chem. 74 2009 4422 4425
16. Y. Geng, D.E. Discher, J. Justynska, and H. Schlaad Angew. Chem., Int. Ed. 118 2006 7740 7743
17. Angew. Chem., Int. Ed. 2006, 45, 7578-7581
18. A. Dondoni, and A. Marra Chem. Soc. Rev. 41 2012 573 586
19. M.S. Kharasch, J. Read, and F.R. Mayo Chem. Ind. (London) 57 1938 752 756
20. C.K. Prier, D.A. Rankic, and D.W.C. MacMillan Chem. Rev. 113 2013 5322 5363
21. J.W. Tucker, and C.R.J. Stephenson J. Org. Chem. 77 2012 1617 1622
22. T.P. Yoon, M.A. Ischay, and J. Du Nat. Chem. 2 2010 527 532
23. J.M.R. Narayanam, and C.R.J. Stephenson Chem. Soc. Rev. 40 2011 102 113
24. F. Teplý Collect. Czech. Chem. Commun. 76 2011 859 917
25. K. Kalyanasundaram Coord. Chem. Rev. 46 1982 159 244
26. A. Juris, V. Balzani, F. Barigelletti, S. Campagna, P. Belser, and V. Von Zelewsky Coord. Chem. Rev. 84 1988 85 277
27. E.L. Tyson, M.S. Ament, and T.P. Yoon J. Org. Chem. 78 2013 2046 2050
28. E.L. Tyson, Z.L. Niemeyer, and T.P. Yoon J. Org. Chem. 79 2014 1427 1436
29. F. Dénès, M. Pichowicz, G. Povie, and P. Renaud Chem. Rev. 2014 10.1021/cr400441m
30. R.O. Recknagel, E.A. Glende Jr., and A.M. Hruszkewycz Chemical Mechanisms in Carbon Tetrachloride Toxicity W.A. Pryor, Free Radicals in Biology Vol. 3 1977 Academic New York, NY 106
31. K. Qvortrup, D.A. Rankic, and D.W.C. MacMillan J. Am. Chem. Soc. 136 2013 626 629
32. A. Fava, G. Reichenbach, and U. Peron J. Am. Chem. Soc. 89 1967 6696 6700
33. H.H. Szmant, A.J. Mata, A.J. Namis, and A.M. Panthananickal Tetrahedron 32 1976 2665 2680
34. V.T. D'Souza, R. Nanjundiah, J. Baeza, and H.H. Szmant J. Org. Chem. 52 1987 1720 1725
35. V.T. D'Souza, V.K. Iyer, and H.H. Szmant J. Org. Chem. 52 1987 1725 1728
36. A. Ma, L. Velazquez, V. Martinez, V. Abrego, M.A. Balboa, L.A. Torres, B. Camacho, S. Diaz-Barriga, A. Romero, R. Lopez-Castanares, and E. Angeles Eur. J. Med. Chem. 43 2008 486 500
37. M. Biava, G.C. Porretta, G. Poce, C. Battilocchio, S. Alfonso, A.D. Logu, N. Serra, F. Manetti, and M. Botta Bioorg. Med. Chem. 18 2010 8076 8084
38. Y. Itoh, A. Yamazaki, Y. Ukai, Y. Yoshikuni, and K. Kimura Pharmacol. Toxicol. 78 1996 421 428
39. Brodney, M. A.; Helal, C. J.; Bronk, B. S.; Liras, S. WO Patent 107808, 2005.
40. Billot, X.; Colucci, J.; Han, Y.; Wilson, M.- C. U.S. Patent 0,227,969, 2005.
41. D.L. Gray, W. Xu, B.M. Campbell, A.B. Dounay, N. Barta, S. Boroski, L. Denny, L. Evans, N. Stratman, and A. Probert Bioorg. Med. Chem. Lett. 19 2009 6640 6670
42. S. Marcaccini, R. Pepino, T. Torroba, D. Miguel, and M.G. Valverde Tetrahedron Lett. 43 2002 8591 8593
43. Z. Liu, and A. Nefzi Tetrahedron Lett. 53 2012 1013 1014
44. H. Zuo, Z.B. Li, F.K. Ren, J.R. Falck, M. Lijuan, C. Ahn, and D.S. Shin Tetrahedron 64 2008 9669 9674
45. D. Chen, Z.H. Wang, and W. Bao J. Org. Chem. 75 2010 5768 5771
46. A.J. Williams, S. Chakthong, D. Gray, R.M. Lawrence, and T. Gallagher Org. Lett. 5 2003 811 814
47. N. Franceschini, S. Da Nascimento, P. Sonnet, and D. Guillaume Tetrahedron: Asymmetry 14 2003 3401 3405
48. N. Ohmura, A. Nakamura, A. Hamasaki, and M. Tokunaga Eur. J. Org. Chem. 2008 5042 5045
49. A.M. Magerramov, A.M. Allakhverdiev, Z.I. Akhmedova, R. Caple, and V.V. Zhdankin Synth. Commun. 29 1999 721 728