Decarboxylative 1,4-Addition of α-Oxocarboxylic Acids with Michael Acceptors Enabled by Photoredox Catalysis

Organic Letters

Volumn 17, Issue 19, 2015, Pages 4830-4833

  Wang, Guang Zu ^a   Shang, Rui ^a   Cheng, Wan Min ^a   Fu, Yao ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84942879223     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b02392     Document Type: Article

References (57)

1. Harutyunyan, S. R.; den Hartog, T.; Geurts, K.; Minnaard, A. J.; Feringa, B. L. Chem. Rev. 2008, 108, 2824 10.1021/cr068424k
2. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992.
3. Schmalz, H.-G. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, Chapter 1.5.
4. Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511 10.1039/c2cs15333e
5. Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606 10.1021/cr068372z
6. Stetter, H.; Kuhlmann, H. Org. React. 1991, 40, 407
7. Stetter, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 639 10.1002/anie.197606391
8. Stetter, H.; Schreckenberg, M. Angew. Chem., Int. Ed. Engl. 1973, 12, 81 10.1002/anie.197300811
9. Fromm, A.; Wüllen, C. V.; Hackenberger, D.; Goossen, L. J. J. Am. Chem. Soc. 2014, 136, 10007 10.1021/ja503295x
10. Song, B.; Knauber, T.; Goossen, L. J. Angew. Chem., Int. Ed. 2013, 52, 2954 10.1002/anie.201208025
11. Feng, Y.-S.; Xu, Z.-Q.; Mao, L.; Zhang, F.-F.; Xu, H.-J. Org. Lett. 2013, 15, 1472 10.1021/ol400197y
12. Shang, R.; Huang, Z.; Xiao, X.; Lu, X.; Fu, Y.; Liu, L. Adv. Synth. Catal. 2012, 352, 2465 10.1002/adsc.201200383
13. Hu, P.; Shang, Y.-P.; Su, W.-P. Angew. Chem., Int. Ed. 2012, 51, 5945 10.1002/anie.201200153
14. Hu, P.; Zhang, M.; Jie, X.-M.; Su, W.-P. Angew. Chem., Int. Ed. 2012, 51, 227 10.1002/anie.201106451
15. Liu, X.; Wang, Z.; Cheng, X.; Li, C. J. Am. Chem. Soc. 2012, 134, 14330 10.1021/ja306638s
16. Rodriguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030 10.1039/c1cs15093f
17. Shang, R.; Liu, L. Sci. China: Chem. 2011, 54, 1670 10.1007/s11426-011-4381-0
18. Shang, R.; Ji, D.-S.; Chu, L.; Fu, Y.; Liu, L. Angew. Chem., Int. Ed. 2011, 50, 4470 10.1002/anie.201006763
19. Shang, R.; Huang, Z.; Chu, L.; Fu, Y.; Liu, L. Org. Lett. 2011, 13, 4240 10.1021/ol201750s
20. Shang, R.; Xu, Q.; Jiang, Y.-Y.; Wang, Y.; Liu, L. Org. Lett. 2010, 12, 1000 10.1021/ol100008q
21. Weaver, J. D.; Ka, B. J.; Morris, D. K.; Thompson, W.; Tunge, J. A. J. Am. Chem. Soc. 2010, 132, 12179 10.1021/ja104196x
22. Shang, R.; Yang, Z.-W.; Wang, Y.; Zhang, S.-L.; Liu, L. J. Am. Chem. Soc. 2010, 132, 14391 10.1021/ja107103b
23. Shang, R.; Fu, Y.; Wang, Y.; Xu, Q.; Yu, H.-Z.; Liu, L. Angew. Chem., Int. Ed. 2009, 48, 9350 10.1002/anie.200904916
24. Shang, R.; Fu, Y.; Li, J.-B.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2009, 131, 5738 10.1021/ja900984x
25. Bi, H.-P.; Zhao, L.; Liang, Y.-M.; Li, C.-J. Angew. Chem., Int. Ed. 2009, 48, 792 10.1002/anie.200805122
26. Waetzig, S. R.; Tunge, J. A. J. Am. Chem. Soc. 2007, 129, 14860 10.1021/ja077070r
27. Chudasama, V.; Fitzmaurice, R. J.; Caddick, S. Nat. Chem. 2010, 2, 592 10.1038/nchem.685
28. Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991 10.1021/cr9601425
29. Rodrĺguez, N.; Manjolinho, F.; Grünberg, M. F.; Goossen, L. J. Chem.-Eur. J. 2011, 17, 13688 10.1002/chem.201102584
30. Goossen, L. J.; Rudolphi, F.; Oppel, C.; Rodríguez, N. Angew. Chem., Int. Ed. 2008, 47, 3043 10.1002/anie.200705127
31. Fontana, F.; Minisci, F.; Nogueira Barbosa, M. C.; Vismara, E. J. Org. Chem. 1991, 56, 2866 10.1021/jo00008a050
32. Yan, K.; Yang, D.; Wei, W.; Wang, F.; Shuai, Y.; Li, Q.; Wang, H. J. Org. Chem. 2015, 80, 1550 10.1021/jo502474z
33. Wang, H.; Guo, L.-N.; Wang, S.; Duan, X.-H. Org. Lett. 2015, 17, 3054 10.1021/acs.orglett.5b01336
34. Walling, C.; Briggs, E. R. J. Am. Chem. Soc. 1946, 68, 1141 10.1021/ja01211a001
35. Shang, R.; Liu, L. Sci. China: Chem. 2011, 54, 1670 10.1007/s11426-011-4381-0
36. Rodriguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030 10.1039/c1cs15093f
37. Goossen, L. J.; Zimmermann, B.; Knauber, T. Angew. Chem., Int. Ed. 2008, 47, 7103 10.1002/anie.200800728
38. Cheng, W.-M.; Shang, R.; Yu, H.-Z.; Fu, Y. Chem.-Eur. J. 2015, 21, 13191 10.1002/chem.201502286
39. Chu, L.-L.; Lipshultz, J.-M.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2015, 54, 7929 10.1002/anie.201501908
40. Huang, H.-C.; Zhang, G.-J.; Chen, Y. Angew. Chem., Int. Ed. 2015, 54, 7872 10.1002/anie.201502369
41. Tan, H.; Li, H.-J.; Ji, W.-Q.; Wang, L. Angew. Chem., Int. Ed. 2015, 54, 8374 10.1002/anie.201503479
42. Zhou, Q.-Q.; Guo, W.; Ding, W.; Wu, X.; Chen, X.; Lu, L.-Q.; Xiao, W.-J. Angew. Chem. 2015, 10.1002/anie.201504559
43. Cuthbertson, J. D.; MacMillan, D. W. C. Nature 2015, 519, 74 10.1038/nature14255
44. Du, J.; Skubi, K. L.; Schultz, D. M.; Yoon, T. P. Science 2014, 344, 392 10.1126/science.1251511
45. Zuo, Z.-W.; Ahneman, D. T.; Chu, L.-L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437 10.1126/science.1255525
46. Tellis, J. C.; Primer, D. N.; Molander, G. A. Science 2014, 345, 433 10.1126/science.1253647
47. Hari, D. P.; König, B. Chem. Commun. 2014, 50, 6688 10.1039/C4CC00751D
48. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322 10.1021/cr300503r
49. Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102 10.1039/B913880N
50. Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77 10.1126/science.1161976
51. Chu, L.-L.; Ohta, C.; Zuo, Z.-W.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 10886 10.1021/ja505964r
52. Miyake, Y.; Nakajima, K.; Nishibayashi, Y. Chem. Commun. 2013, 49, 7854 10.1039/c3cc44438d
53. Generally, simple alkyl and benzyl radicals have lower redox potentials [E1/2(M¢/M-)] compared with α-carbonyl radicals. For a reference on redox potentials of organic free radicals, see: Fu, Y.; Liu, L.; Yu, H.-Z.; Wang, Y.-M.; Guo, Q.-X. J. Am. Chem. Soc. 2005, 127, 7227 10.1021/ja0421856
54. Nguyen, J. D.; D'Amato, E. M.; Narayanam, J. M. R.; Stephenson, C. R. J. Nat. Chem. 2012, 4, 854 10.1038/nchem.1452
55. Kim, H.; Lee, C. Angew. Chem., Int. Ed. 2012, 51, 12303 10.1002/anie.201203599
56. Mattson, A. E.; Bharadwaj, A. R.; Zuhl, A. M.; Scheidt, K. A. J. Org. Chem. 2006, 71, 5715 10.1021/jo060699c
57. Bharadwaj, A. R.; Scheidt, K. A. Org. Lett. 2004, 6, 2465 10.1021/ol049044t