Alkyne Difunctionalization by Dual Gold/Photoredox Catalysis

Chemistry - A European Journal

Volumn 22, Issue 17, 2016, Pages 5909-5913

  Tlahuext Aca, Adrian ^a   Hopkinson, Matthew N ^a   Aleyda Garza Sanchez, R ^a   Glorius, Frank ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

alkynes; arylation; diazonium salts; gold; synthetic methods

Indexed keywords

ADDITION REACTIONS; CATALYSIS; HYDROCARBONS; LIGHT;

ALKYNES; ARYLATIONS; CROSS-COUPLED PRODUCT; DIAZONIUM SALTS; DIFUNCTIONALIZATION; NUCLEOPHILIC ADDITIONS; SYNTHETIC METHODS; VISIBLE LIGHT ACTIVATIONS;

GOLD;

EID: 84960145256     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201600710     Document Type: Article

References (82)

1. A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. Int. Ed. 2006, 45, 7896;
2. Angew. Chem. 2006, 118, 8064;
3. D. J. Gorin, F. D. Toste, Nature 2007, 446, 395;
4. A. Fürstner, Chem. Soc. Rev. 2009, 38, 3208;
5. N. Krause, C. Winter, Chem. Rev. 2011, 111, 1994;
6. M. Bandini, Chem. Soc. Rev. 2011, 40, 1358;
7. M. Rudolph, A. S. K. Hashmi, Chem. Soc. Rev. 2012, 41, 2448;
8. R. Dorel, A. M. Echavarren, Chem. Rev. 2015, 115, 9028.
9. Y. Shi, S. M. Peterson, W. W. Haberaecker III, S. A. Blum, J. Am. Chem. Soc. 2008, 130, 2168;
10. A. S. K. Hashmi, C. Lothschütz, R. Döpp, M. Rudolph, T. D. Ramamurthi, F. Rominger, Angew. Chem. Int. Ed. 2009, 48, 8243;
11. Angew. Chem. 2009, 121, 8392;
12. Y. Shi, S. D. Ramgren, S. A. Blum, Organometallics 2009, 28, 1275;
13. A. S. K. Hashmi, C. Lothschütz, R. Döpp, M. Ackermann, J. D. B. Becker, M. Rudolph, C. Scholz, F. Rominger, Adv. Synth. Catal. 2012, 354, 133; nickel:
14. J. J. Hirner, S. A. Blum, Organometallics 2011, 30, 1299; rhodium:
15. Y. Shi, S. A. Blum, Organometallics 2011, 30, 1776; iron and ruthenium:
16. A. S. K. Hashmi, L. Molinari, Organometallics 2011, 30, 3457; halogens:
17. A. Buzas, F. Gagosz, Org. Lett. 2006, 8, 515;
18. A. S. K. Hashmi, T. D. Ramamurthi, F. Rominger, J. Organomet. Chem. 2009, 694, 592;
19. B. Gockel, N. Krause, Eur. J. Org. Chem. 2010, 311;
20. F. Mo, J. M. Yan, D. Qiu, F. Li, Y. Zhang, J. Wang, Angew. Chem. Int. Ed. 2010, 49, 2028;
21. Angew. Chem. 2010, 122, 2072;
22. D. Qiu, F. Mo, Z. Zheng, Y. Zhang, J. Wang, Org. Lett. 2010, 12, 5474;
23. M. Schuler, F. Silva, C. Bobbio, A. Tessier, V. Gouverneur, Angew. Chem. Int. Ed. 2008, 47, 7927;
24. Angew. Chem. 2008, 120, 8045.
25. M. N. Hopkinson, A. D. Gee, V. Gouverneur, Chem. Eur. J. 2011, 17, 8248;
26. H. A. Wegner, M. Auzias, Angew. Chem. Int. Ed. 2011, 50, 8236;
27. Angew. Chem. 2011, 123, 8386.
28. S. G. Bratsch, J. Chem. Phys. Ref. Data 1989, 18, 1.
29. R. L. LaLonde, W. E. Brenzovich Jr., D. Benitez, E. Tkatchouk, K. Kelley, W. A. Goddard III, F. D. Toste, Chem. Sci. 2010, 1, 226;
30. L.-P. Liu, B. Xu, M. S. Mashuta, G. B. Hammond, J. Am. Chem. Soc. 2008, 130, 17642. Reviews:
31. A. S. K. Hashmi, Angew. Chem. Int. Ed. 2010, 49, 5232;
32. Angew. Chem. 2010, 122, 5360;
33. L.-P. Liu, G. B. Hammond, Chem. Soc. Rev. 2012, 41, 3129.
34. T. P. Yoon, M. A. Ischay, J. Du, Nat. Chem. 2010, 2, 527;
35. J. M. R. Narayanam, C. R. J. Stephenson, Chem. Soc. Rev. 2011, 40, 102;
36. J. Xuan, W.-J. Xiao, Angew. Chem. Int. Ed. 2012, 51, 6828;
37. Angew. Chem. 2012, 124, 6934;
38. C. K. Prier, D. A. Rankic, D. W. C. MacMillan, Chem. Rev. 2013, 113, 5322;
39. M. Reckenthäler, A. G. Griesbeck, Adv. Synth. Catal. 2013, 355, 2727;
40. D. M. Schultz, T. P. Yoon, Science 2014, 343, 1239176;
41. D. A. Nicewicz, T. M. Nguyen, ACS Catal. 2014, 4, 355;
42. M. N. Hopkinson, B. Sahoo, J.-L. Li, F. Glorius, Chem. Eur. J. 2014, 20, 3874;
43. E. Meggers, Chem. Commun. 2015, 51, 3290;
44. R. A. Angnes, Z. Li, C. R. D. Correia, G. B. Hammond, Org. Biomol. Chem. 2015, 13, 9152. Examples of gold complexes as photoredox catalysts:
45. G. Revol, T. McCallum, M. Morin, F. Gagosz, L. Barriault, Angew. Chem. Int. Ed. 2013, 52, 13342;
46. Angew. Chem. 2013, 125, 13584;
47. J. Xie, S. Shi, T. Zhang, N. Mehrkens, M. Rudolph, A. S. K. Hashmi, Angew. Chem. Int. Ed. 2015, 54, 6046;
48. Angew. Chem. 2015, 127, 6144.
49. B. Sahoo, M. N. Hopkinson, F. Glorius, J. Am. Chem. Soc. 2013, 135, 5505;
50. M. N. Hopkinson, B. Sahoo, F. Glorius, Adv. Synth. Catal. 2014, 356, 2794;
51. X.-Z. Shu, M. Zhang, Y. He, H. Frei, F. D. Toste, J. Am. Chem. Soc. 2014, 136, 5844;
52. D. V. Patil, H. Yun, S. Shin, Adv. Synth. Catal. 2015, 357, 2622.
53. Y. He, H. Wu, F. D. Toste, Chem. Sci. 2015, 6, 1194;
54. A. Tlahuext-Aca, M. N. Hopkinson, B. Sahoo, F. Glorius, Chem. Sci. 2016, 7, 89;
55. S. Kim, J. Rojas-Martin, F. D. Toste, Chem. Sci. 2016, 7, 85.
56. D. A. Engel, G. B. Dudley, Org. Biomol. Chem. 2009, 7, 4149. Selected reports on the gold-catalyzed formation of α-functionalized enones based on the Meyer-Schuster or related rearrangement reactions:
57. M. Yu, G. Zhang, L. Zhang, Org. Lett. 2007, 9, 2147;
58. G. Zhang, Y. Peng, L. Cui, L. Zhang, Angew. Chem. Int. Ed. 2009, 48, 3112;
59. Angew. Chem. 2009, 121, 3158;
60. L. Ye, L. Zhang, Org. Lett. 2009, 11, 3646;
61. M. Yu, G. Zhang, L. Zhang, Tetrahedron 2009, 65, 1846;
62. Y. Peng, L. Cui, G. Zhang, L. Zhang, J. Am. Chem. Soc. 2009, 131, 5062;
63. M. N. Hopkinson, G. T. Giuffredi, A. D. Gee, V. Gouverneur, Synlett 2010, 2737;
64. D. Wang, X. Ye, X. Shi, Org. Lett. 2010, 12, 2088;
65. T. deHaro, C. Nevado, Chem. Commun. 2011, 47, 248;
66. N. Marion, S. Díez-González, P. deFrémont, A. R. Noble, S. P. Nolan, Angew. Chem. Int. Ed. 2006, 45, 3647;
67. Angew. Chem. 2006, 118, 3729;
68. Y. Yu, W. Yang, D. Pflästerer, A. S. K. Hashmi, Angew. Chem. Int. Ed. 2014, 53, 1144;
69. Angew. Chem. 2014, 126, 1162.
70. W. Wang, J. Jasinski, G. B. Hammond, B. Xu, Angew. Chem. Int. Ed. 2010, 49, 7247;
71. Angew. Chem. 2010, 122, 7405;
72. T. deHaro, C. Nevado, Adv. Synth. Catal. 2010, 352, 2767;
73. B. Xu, W. Wang, G. B. Hammond, J. Fluorine Chem. 2011, 132, 804.
74. J. A. Goodwin, A. Aponick, Chem. Commun. 2015, 51, 8730.
75. D. P. Hari, B. König, Angew. Chem. Int. Ed. 2013, 52, 4734;
76. Angew. Chem. 2013, 125, 4832.
77. 3 radical:
78. M. S. Winston, W. J. Wolf, F. D. Toste, J. Am. Chem. Soc. 2014, 136, 7777. For a recent theoretical study on dual gold/photoredox catalysis, see:
79. Q. Zhang, Z.-Q. Zhang, Y. Fu, H.-Z. Yu, ACS Catal. 2016, 6, 798.
80. M. Majek, F. Filace, A. J. vonWangelin, Beilstein J. Org. Chem. 2014, 10, 981;
81. M. A. Cismesia, T. P. Yoon, Chem. Sci. 2015, 6, 5426.
82. During the submission of this manuscript, Shin and co-workers reported a related dual gold/photoredox catalyzed arylative Meyer-Schuster rearrangement, see:, J. Um, H. Yun, S. Shin, Org. Lett. 2016, 18, 484.