Photocatalytic Decarboxylative Hydroxylation of Carboxylic Acids Driven by Visible Light and Using Molecular Oxygen

Journal of Organic Chemistry

Volumn 81, Issue 16, 2016, Pages 7250-7255

  Song, Hai Tao ^a   Ding, Wei ^a   Zhou, Quan Quan ^a   Liu, Jing ^a   Lu, Liang Qiu ^a   Xiao, Wen Jing ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; HYDROXYLATION; LIGHT;

DRIVING FORCES; GREEN OXIDANTS; HIGH YIELD; MILD REACTION CONDITIONS; PHOTO-CATALYTIC; VISIBLE LIGHT;

MOLECULAR OXYGEN;

ALCOHOL DERIVATIVE; CARBOXYLIC ACID; OXYGEN;

ARTICLE; CATALYST; CHEMICAL BOND; CONTROLLED STUDY; DECARBOXYLATION; FORCE; HYDROXYLATION; LIGHT; PHOTOCATALYSIS; REACTION TIME; STOICHIOMETRY;

EID: 84983261893     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.6b01360     Document Type: Article

References (58)

1. Tsuji, H.; Ogawa, T.; Bando, N.; Sasaoka, K. J. Biol. Chem. 1986, 261, 13203
2. Mizutani, Y.; Narikawa, T.; Satoh, T.; Sakurai, N.; Kaji, H.; Yamada, S.; Samejima, T. J. Biochem. 1999, 126, 347 10.1093/oxfordjournals.jbchem.a022456
3. Totah, R. A.; Hanzlik, R. P. J. Am. Chem. Soc. 2002, 124, 10000 10.1021/ja020559u
4. Uemura, T.; Kita, A.; Watanabe, Y.; Adachi, M.; Kuroki, R.; Morimoto, Y. Biochem. Biophys. Res. Commun. 2016, 469, 158 10.1016/j.bbrc.2015.11.087
5. Wo, J.; Kong, D.-K.; Brock, N. L.; Xu, F.; Zhou, X.-F.; Deng, Z.-X.; Lin, S.-J. ACS Catal. 2016, 6, 2831 10.1021/acscatal.6b00154
6. Corey, E. J.; Casanova, J. J. Am. Chem. Soc. 1963, 85, 165 10.1021/ja00885a013
7. Kochi, J. K.; Bacha, J. D.; Bethea, T. W. J. Am. Chem. Soc. 1967, 89, 6538 10.1021/ja01001a029
8. Anderson, J. M.; Kochi, J. K. J. Am. Chem. Soc. 1970, 92, 2450 10.1021/ja00711a041
9. Kochi, J. K.; Bethea, T. W. J. Org. Chem. 1968, 33, 75 10.1021/jo01265a015
10. Anderson, J.; Kochi, J. K. J. Org. Chem. 1970, 35, 986 10.1021/jo00829a026
11. Mirkhani, V.; Tangestaninejad, S.; Moghadam, M.; Moghbel, M. Bioorg. Med. Chem. 2004, 12, 903 10.1016/j.bmc.2003.12.025
12. Haldar, P.; Ray, J. K. Tetrahedron Lett. 2008, 49, 3659 10.1016/j.tetlet.2008.03.147
13. Kiyokawa, K.; Yahata, S.; Kojima, T.; Minakata, S. Org. Lett. 2014, 16, 4646 10.1021/ol5022433
14. 2 at 120 °C, see: Feng, Q.; Song, Q. J. Org. Chem. 2014, 79, 1867 10.1021/jo402778p
15. Barton, D. H. R. Half a Century of Free Radical Chemistry; Cambridge University Press: Cambridge, 1993.
16. Crich, D.; Quintero, L. Chem. Rev. 1989, 89, 1413 10.1021/cr00097a001
17. Barton, D. H. R.; Zard, S. Z. Pure Appl. Chem. 1986, 58, 675 10.1351/pac198658050675
18. Barton, D. H. R.; Crich, D.; Motherwell, W. B. J. Chem. Soc., Chem. Commun. 1984, 242 10.1039/c39840000242
19. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901 10.1016/S0040-4020(01)97173-X
20. Barton, D. H. R.; Géro, S. D.; Holliday, P.; Quiclet-Sire, B.; Zard, S. Z. Tetrahedron 1998, 54, 6751 10.1016/S0040-4020(98)00337-8
21. Breder, A.; Chinigo, G. M.; Waltman, A. W.; Carreira, E. M. Chem.-Eur. J. 2011, 17, 12405 10.1002/chem.201101862
22. Asaba, T.; Katoh, Y.; Urabe, D.; Inoue, M. Angew. Chem., Int. Ed. 2015, 54, 14457 10.1002/anie.201509160
23. Liu, C.; Wang, X.; Li, Z.; Cui, L.; Li, C. J. Am. Chem. Soc. 2015, 137, 9820 10.1021/jacs.5b06821
24. For a selected review, see: Xuan, J.; Zhang, Z.-G.; Xiao, W.-J. Angew. Chem., Int. Ed. 2015, 54, 15632 10.1002/anie.201505731
25. Huang, H.; Zhang, G.; Chen, Y. Angew. Chem., Int. Ed. 2015, 54, 7872 10.1002/anie.201502369
26. Tan, H.; Li, H.; Ji, W.; Wang, L. Angew. Chem., Int. Ed. 2015, 54, 8374 10.1002/anie.201503479
27. Zhou, Q.-Q.; Guo, W.; Ding, W.; Wu, X.; Chen, X.; Lu, L.-Q.; Xiao, W.-J. Angew. Chem., Int. Ed. 2015, 54, 11196 10.1002/anie.201504559
28. Wang, G.-Z.; Shang, R.; Cheng, W.-M.; Fu, Y. Org. Lett. 2015, 17, 4830 10.1021/acs.orglett.5b02392
29. Ventre, S.; Petronijevic, F. R.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 5654 10.1021/jacs.5b02244
30. Zhou, C.; Li, P.-H.; Zhu, X.-J.; Wang, L. Org. Lett. 2015, 17, 6198 10.1021/acs.orglett.5b03192
31. Le Vaillant, F.; Courant, T.; Waser, J. Angew. Chem., Int. Ed. 2015, 54, 11200 10.1002/anie.201505111
32. Griffin, J. D.; Zeller, M. A.; Nicewicz, D. A. J. Am. Chem. Soc. 2015, 137, 11340 10.1021/jacs.5b07770
33. Candish, L.; Pitzer, L.; Gomez-Suarez, A.; Glorius, F. Chem.-Eur. J. 2016, 22, 4753 10.1002/chem.201600421
34. Capaldo, L.; Buzzetti, L.; Merli, D.; Fagnoni, M.; Ravelli, D. J. Org. Chem. 2016, 10.1021/acs.joc.6b00984
35. Narayanam, J. M.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102 10.1039/B913880N
36. Shi, L.; Xia, W. Chem. Soc. Rev. 2012, 41, 7687 10.1039/c2cs35203f
37. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322 10.1021/cr300503r
38. Nicewicz, D. A.; Nguyen, T. M. ACS Catal. 2014, 4, 355 10.1021/cs400956a
39. Schultz, D. M.; Yoon, T. P. Science 2014, 343, 985 10.1126/science.1239176
40. Ravelli, D.; Protti, S.; Fagnoni, M. Chem. Rev. 2016, 10.1021/acs.chemrev.5b00662
41. Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 10.1021/acs.chemrev.6b00057
42. Xuan, J.; Xia, X.-D.; Zeng, T.-T.; Feng, Z.-J.; Chen, J.-R.; Lu, L.-Q.; Xiao, W.-J. Angew. Chem., Int. Ed. 2014, 53, 5653 10.1002/anie.201400602
43. Xuan, J.; Feng, Z.-J.; Chen, J.-R.; Lu, L.-Q.; Xiao, W.-J. Chem.-Eur. J. 2014, 20, 3045 10.1002/chem.201304898
44. Xuan, J.; Zeng, T.-T.; Feng, Z.-J.; Deng, Q.-H.; Chen, J.-R.; Lu, L.-Q.; Xiao, W.-J.; Alper, H. Angew. Chem., Int. Ed. 2015, 54, 1625 10.1002/anie.201409999
45. Guo, W.; Lu, L.-Q.; Wang, Y.; Wang, Y.-N.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2015, 54, 2265 10.1002/anie.201408837
46. Zeng, T.-T.; Xuan, J.; Ding, W.; Wang, K.; Lu, L.-Q.; Xiao, W.-J. Org. Lett. 2015, 17, 4070 and 8c. 10.1021/acs.orglett.5b01994
47. Rieu, J. P.; Boucherle, A.; Cousse, H.; Mouzin, G. Tetrahedron 1986, 42, 4095 10.1016/S0040-4020(01)87634-1
48. Pan, Y.; Wang, S.; Kee, C. W.; Dubuisson, E.; Yang, Y.; Loh, K. P.; Tan, C.-H. Green Chem. 2011, 13, 3341 10.1039/c1gc15865a
49. Ohkubo, K.; Suga, K.; Morikawa, K.; Fukuzumi, S. J. Am. Chem. Soc. 2003, 125, 12850 10.1021/ja036645r
50. Kotani, H.; Ohkubo, K.; Fukuzumi, S. J. Am. Chem. Soc. 2004, 126, 15999 10.1021/ja048353b
51. Cassani, C.; Bergonzini, G.; Wallentin, C.-J. Org. Lett. 2014, 16, 4228 10.1021/ol5019294
52. Chinzei, T.; Miyazawa, K.; Yasu, Y.; Koike, T.; Akita, M. RSC Adv. 2015, 5, 21297 10.1039/C5RA01826A
53. Wu, X.-X.; Meng, C.-N.; Yuan, X.-Q.; Jia, X.-T.; Qian, X.-H.; Ye, J.-X. Chem. Commun. 2015, 51, 11864 10.1039/C5CC04527D
54. Wang, K.; Meng, L.-G.; Zhang, Q.; Wang, L. Green Chem. 2016, 18, 2864 10.1039/C5GC02550H
55. Su, Y.-J.; Zhang, L.-R.; Jiao, N. Org. Lett. 2011, 13, 2168 10.1021/ol2002013
56. Yi, H.; Bian, C.-L.; Hu, X.; Niu, L.-B.; Lei, A. Chem. Commun. 2015, 51, 14046 10.1039/C5CC06015J
57. Jung, J.; Kim, J.; Park, G.; You, Y.-M.; Cho, E. J. Adv. Synth. Catal. 2016, 358, 74 10.1002/adsc.201500734
58. Wang, H.-M.; Lu, Q.-Q.; Qian, C. H.; Liu, C.; Liu, W.; Chen, K.; Lei, A. Angew. Chem., Int. Ed. 2016, 55, 1094 10.1002/anie.201508729