Fragment Coupling and the Construction of Quaternary Carbons Using Tertiary Radicals Generated from tert -Alkyl N -Phthalimidoyl Oxalates by Visible-Light Photocatalysis

Journal of Organic Chemistry

Volumn 80, Issue 12, 2015, Pages 6012-6024

  Lackner, Gregory L ^a   Quasdorf, Kyle W ^a   Pratsch, Gerald ^a   Overman, Larry E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS; HYDROCARBONS; LIGHT; REACTION INTERMEDIATES; SUBSTITUTION REACTIONS;

DEUTERIUM LABELING; ELECTRON-DEFICIENT; HYDROGEN-ATOM TRANSFER; QUATERNARY CARBON; REDUCTIVE COUPLINGS; TERTIARY ALCOHOLS; TERTIARY RADICALS; VISIBLE-LIGHT PHOTOCATALYSIS;

FREE RADICAL REACTIONS;

ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; CARBON; DEUTERIUM; HALIDE; HYDROGEN; OXALIC ACID DERIVATIVE; RADICAL; 1-(4-BROMO-1H-PYRROL-2-YL)-2,2,2-TRICHLOROETHANONE; CATION; CHLOROETHANE; ETHYL 4-(4-CYANO-1-METHYL-1H-IMIDAZOL-5-YL)-1-ETHYL-1H-PYRROLE-2-CARBOXYLATE; IMIDAZOLE DERIVATIVE; PHTHALIMIDE DERIVATIVE; PYRROLE DERIVATIVE;

ACYLATION; ARTICLE; CONTROLLED STUDY; LIGHT; PHOTOCATALYSIS; SUBSTITUTION REACTION; SYNTHESIS; ANALOGS AND DERIVATIVES; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; PHOTOCHEMISTRY;

CARBON; CATALYSIS; ETHYL CHLORIDE; IMIDAZOLES; LIGHT; MOLECULAR STRUCTURE; ONIUM COMPOUNDS; OXALATES; PHOTOCHEMICAL PROCESSES; PHTHALIMIDES; PYRROLES;

EID: 84935033940     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00794     Document Type: Article

References (72)

1. Schnermann, M. J.; Untiedt, N. L.; Jimenez-Oses, G.; Houk, K. N.; Overman, L. E. Angew. Chem., Int. Ed. 2012, 51, 9581-9586
2. Schnermann, M. J.; Overman, L. E. Angew. Chem., Int. Ed. 2012, 51, 9576-9580
3. Müller, D. S.; Untiedt, N. L.; Dieskau, A. P.; Lackner, G. L.; Overman, L. E. J. Am. Chem. Soc. 2015, 137, 660-663
4. Gaoni, Y. Tetrahedron 1989, 45, 2819-2840
5. Mandelt, K.; Meyer-Wilmes, I.; Fitjer, L. Tetrahedron 2004, 60, 11587-11595
6. Hodgson, D. M.; Chung, Y. K.; Nuzzo, I.; Freixas, G.; Kulikiewicz, K. K.; Cleator, E.; Paris, J. M. J. Am. Chem. Soc. 2007, 129, 4456-4462
7. Joshi-Pangu, A.; Wang, C.-Y.; Biscoe, M. R. J. Am. Chem. Soc. 2011, 133, 8478-8481
8. Ren, P.; Stern, L.-A.; Hu, X. Angew. Chem., Int. Ed. 2012, 51, 9110-9113
9. Iwasaki, T.; Takagawa, H.; Singh, S. P.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2013, 135, 9604-9607
10. Leonori, D.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2015, 54, 1082-1096
11. Furst, L.; Narayanam, J. M. R.; Stephenson, C. R. J. Angew. Chem., Int. Ed. 2011, 50, 9655-9659
12. Lackner, G. L.; Quasdorf, K. W.; Overman, L. E. J. Am. Chem. Soc. 2013, 135, 15342-15345
13. Lo, J. C.; Yabe, Y.; Baran, P. S. J. Am. Chem. Soc. 2014, 136, 1304-1307
14. Chu, L.; Ohta, C.; Zuo, Z.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 10886-10889
15. Chinzei, T.; Miyazawa, K.; Yasu, Y.; Koike, T.; Akita, M. RSC Adv. 2015, 5, 21297-21300
16. Barton, D. H. R.; Serebryakov, E. P. A. Proc. Chem. Soc. 1962, 309
17. Barton, D. H. R.; Dowlatshahi, H. A.; Motherwell, W. B.; Villemin, D. J. Chem. Soc., Chem. Commun. 1980, 732-733
18. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron Lett. 1983, 24, 4979-4982
19. Barton, D.; Chern, C.-Y.; Jaszberenyi, J. Tetrahedron 1995, 51, 1867-1886
20. For a brief review, see: Saraiva, M. F.; Couri, M. R. C.; Hyaric, M. L.; de Almeida, M. V. Tetrahedron 2009, 65, 3563-3572
21. Barton, D. H. R.; Crich, D. Tetrahedron Lett. 1985, 26, 757-760
22. Barton, D. H. R.; Crich, D.; Kretzschmar, G. J. Chem. Soc., Perkin Trans. 1 1986, 39-53
23. Other methods include generation of tertiary radicals by photolysis of benzophenone oxime esters, see: Hasebe, M.; Tsuchiya, T. Tetrahedron Lett. 1986, 27, 3239-3242
24. Nugent, W. A.; RajanBabu, T. V. J. Am. Chem. Soc. 1988, 110, 8561-8562
25. Gansäuer, A.; Lauterbach, T.; Narayan, S. Angew. Chem., Int. Ed. 2003, 42, 5556-5573
26. Cuerva, J. M.; Justica, J.; Oller-López, J. L. V.; Enrique Oltra, J. Top. Curr. Chem. 2006, 264, 63-91
27. Okada, K.; Okamoto, K.; Morita, N.; Okubo, K.; Oda, M. J. Am. Chem. Soc. 1991, 113, 9401-9402
28. Mariano, P. S.; Stavinoha, J. L. In Synthetic Organic Photochemistry; Horspool, W. M., Ed.; Plenum Press: NY, USA, 1984; pp 145-257.
29. Eberson, L. Electron Transfer Reactions in Organic Chemistry; Springer-Verlag: NY, 1987.
30. Fagnoni, M.; Dondi, D.; Ravelli, D.; Albini, A. Chem. Rev. 2007, 107, 2725-2756
31. For selected reviews discussing the addition of carbon radicals to alkenes, see: Renaud, P.; Sibi, M. P. Radicals in Organic Synthesis; Wiley-VCH, Weinheim, 2001; Vol. 2.
32. Zard, S. Z. Radical Reactions in Organic Synthesis; Oxford: New York, 2003.
33. Srikanth, G. S. C.; Castle, S. L. Tetrahedron 2005, 61, 10377-10441
34. Rowlands, G. J. Tetrahedron 2009, 65, 8603-8655
35. For a recent disclosure of photocatalytic reductive alkynylation of carbon radicals formed from (N -acyloxy)phthalimides, see: Yang, J.; Zhang, J.; Oi, L.; Hu, C.; Chen, Y. Chem. Commun. 2015, 51, 5275-5278
36. Accompanying article, see: Pratsch, G.; Lackner, G. L.; Overman, L. E. J. Org. Chem. 2015, 10.1021/acs.joc.5b00795
37. Okada reports reduction potentials in the range from -1.28 to -1.37 V (vs SCE) for three (N -acyloxy)phthalimides in acetonitrile, see: Okada, K.; Okamoto, K.; Oda, M. J. Am. Chem. Soc. 1988, 110, 8736-8738
38. Andrews, R. S.; Becker, J. J.; Gagné, M. R. Angew. Chem., Int. Ed. 2010, 49, 7274-7276
39. For a comprehensive review of visible-light photocatalysis, which discusses the reactivity and electrochemical potentials of common photoredox catalysts, see: Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322-5363
40. Zhu, X.-Q.; Li, H.-R.; Li, Q.; Ai, T.; Lu, J.-Y.; Yang, Y.; Cheng, J.-P. Chem.-Eur. J. 2003, 9, 871-880
41. Zhu, X.-Q.; Zhang, M.-T.; Yu, A.; Wang, C.-H.; Cheng, J.-P. J. Am. Chem. Soc. 2008, 130, 2501-2516
42. Zhu, X.-Q.; Tan, Y.; Cao, C.-T. J. Phys. Chem. B 2010, 114, 2058-2075
43. Fukuzimi, S.; Mochizuki, S.; Tanaka, T. J. Phys. Chem. 1990, 94, 722-726
44. -1, see: Togo, H. Advanced Free Radical Reactions for Organic Synthesis; Elsevier Science: Amsterdam, 2004.
45. Rüegge, D.; Fischer, H. Int. J. Chem. Kinet. 1986, 18, 145-158
46. Beckwith, A. L. J.; Bowry, V.; Moad, G. J. Org. Chem. 1988, 53, 1632-1641
47. Simakov, P. A.; Martinez, F. N.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1998, 63, 1226-1232
48. Morihovitis, T.; Schiesser, C. H.; Skidmore, M. A. J. Chem. Soc., Perkin Trans. 2 1999, 2041-2047
49. Togo, H.; Yokoyama, M. Heterocycles 1990, 31, 437-441
50. Togo, H.; Fujii, M.; Yokoyama, M. Bull. Chem. Soc. Jpn. 1991, 64, 57-67
51. Larraufie, M.-H.; Pellet, R.; Fensterbank, L.; Goddard, J.-P.; Lacôte, E.; Malacria, M.; Ollivier, C. Angew. Chem., Int. Ed. 2011, 50, 4463-4466
52. Dai, X.; Cheng, D.; Guan, B.; Mao, W.; Xu, X.; Li, X. J. Org. Chem. 2014, 79, 7212-7219
53. Schäfer, H. Angew. Chem., Int. Ed. 1970, 9, 158-159
54. Kambe, N.; Miyamoto, M.; Terao, J.; Watabe, H. Bull. Chem. Soc. Jpn. 2003, 76, 2209-2214
55. Shen, Z.-L.; Cheong, H.-L.; Loh, T.-P. Tetrahedron Lett. 2009, 50, 1051-1054
56. Bockrath, B.; Bittner, E.; McGrewt, J. J. Am. Chem. Soc. 1984, 106, 135-138
57. Mayer, J. M. Acc. Chem. Res. 2011, 44, 36-46
58. Wille, U. Chem. Rev. 2013, 113, 813-853
59. Crich, D.; Grant, D.; Krishnamurthy, V.; Patel, M. Acc. Chem. Res. 2007, 40, 453-463
60. Norcross, B. E.; Klinedinst, P. E., Jr.; Westheimer, F. H. J. Am. Chem. Soc. 1962, 84, 797-802
61. For recent use of 4,4-dideuterio-Hantzsch esters in studies of reactions promoted by visible-light photoredox catalysis, see: Neumann, M.; Zeitler, K. Chem.-Eur. J. 2013, 19, 6950-6955
62. Fukuzimi, S.; Koumitsu, S.; Hironaka, K.; Tanaka, T. J. Am. Chem. Soc. 1987, 109, 305-316
63. Eey, S. T. C; Lear, M. J. Org. Lett. 2010, 12, 5510-5513
64. Abdel-Mohsen, H. T.; Conrad, J.; Beifuss, U. Green Chem. 2012, 14, 2686-2690
65. Chikashita, H.; Miyazaki, M.; Itoh, K. Synthesis 1984, 4, 308-310
66. Pintér, á.; Sud, A.; Sureshkumar, D.; Klussmann, M. Angew. Chem., Int. Ed. 2010, 49, 5004-5007
67. Huang, H.; Liu, X.; Deng, J.; Qiu, M.; Zheng, Z. Org. Lett. 2006, 8, 3359-3362
68. Kippo, T.; Fukuyama, T.; Ryu, I. Org. Lett. 2011, 13, 3864-3867
69. Young, W. G.; Caserio, F. F., Jr.; Brandon, D. D., Jr. J. Am. Chem. Soc. 1960, 82, 6163-6168
70. Ma, S.; Lu, X.; Li, Z. J. Org. Chem. 1992, 57, 709-713
71. Tripathi, C. B.; Mukherjee, S. Angew. Chem., Int. Ed. 2013, 52, 8450-8453
72. Graff, M.; Al Dilaimi, A.; Seguineau, P.; Rambaud, M.; Villieras, J. Tetrahedron Lett. 1986, 27, 1577-1578