Gold Redox Catalysis through Base-Initiated Diazonium Decomposition toward Alkene, Alkyne, and Allene Activation

Chemistry - A European Journal

Volumn 23, Issue 46, 2017, Pages 11093-11099

  Dong, Boliang ^a   Peng, Haihui ^a   Motika, Stephen E ^a   Shi, Xiaodong ^a  

^a UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

alkenes; alkynes; diazonium salts; gold; photocatalysis

Indexed keywords

CATALYSIS; CHEMICAL ACTIVATION; EFFICIENCY; GOLD; NETWORK SECURITY; OLEFINS; PHOTOCATALYSIS; REACTION RATES; SALTS; SODIUM CARBONATE; SODIUM COMPOUNDS;

ALKYNES; DIAZONIUM SALTS; FASTER REACTIONS; PHOTO-ACTIVATION METHODS; PRACTICAL ISSUES; REACTION CONDITIONS; REDUCTIVE ELIMINATION; VARIOUS SUBSTRATES;

GOLD COMPOUNDS;

EID: 85027512409     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201701970     Document Type: Article

References (121)

1. Selected reviews on Au catalysis:
2. A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180;
3. A. Fürstner, P. W. Davies, Angew. Chem. Int. Ed. 2007, 46, 3410;
4. Angew. Chem. 2007, 119, 3478;
5. D. Gorin, F. D. Toste, Nature 2007, 446, 395;
6. A. Arcadi, Chem. Rev. 2008, 108, 3266;
7. Z. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239;
8. D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351;
9. R. A. Widenhoefer, Chem. Eur. J. 2008, 14, 5382;
10. A. Fürstner, Chem. Soc. Rev. 2009, 38, 3208;
11. N. Krause, C. Winter, Chem. Rev. 2011, 111, 1994;
12. M. Bandini, Chem. Soc. Rev. 2011, 40, 1358;
13. M. N. Hopkinson, A. D. Gee, V. Gouverneur, Chem. Eur. J. 2011, 17, 8248;
14. A. Corma, A. Leyva-Pérez, M. Sabater, Chem. Rev. 2011, 111, 1657;
15. T. de Haro, C. Nevado, Synthesis 2011, 2530;
16. L.-P. Liu, G. B. Hammond, Chem. Soc. Rev. 2012, 41, 3129;
17. L. Zhang, Acc. Chem. Res. 2014, 47, 877;
18. R. Dorel, A. M. Echavarren, Chem. Rev. 2015, 115, 9028;
19. D. Pflästerer, A. S. K. Hashmi, Chem. Soc. Rev. 2016, 45, 1331.
20. E0 (AuI/AuIII)=+1.40 V. See:
21. S. G. S. Bratsch, J. Phys. Chem. Ref. Data 1989, 18, 1;
22. CRC Handbook of Chemistry and Physics, 84th ed.; D. R. Lide, CRC Press, Boca Raton, FL, 2004. For a stable example, including an X-ray crystal structure analysis, of a dicoordinated gold(I) center that does not undergo oxidative addition with an aryl iodide that could intramolecularly react by a six-membered transition state, see:
23. 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.
24. S. Gaillard, A. M. Z. Slawin, A. T. Bonura, E. D. Stevens, S. P. Nolan, Organometallics 2010, 29, 394;
25. W. E. Brenzovich, Jr., D. Benitez, A. D. Lackner, H. P. Shunatona, E. Tkatchouk, W. A. Goddard III, F. D. Toste, Angew. Chem. Int. Ed. 2010, 49, 5519;
26. Angew. Chem. 2010, 122, 5651;
27. A. D. Melhado, W. E. Brenzovich Jr., A. D. Lackner, F. D. Toste, J. Am. Chem. Soc. 2010, 132, 8885;
28. M. N. Hopkinson, A. Tessier, A. Salisbury, G. T. Giuffredi, L. E. Combettes, A. D. Gee, V. Gouverneur, Chem. Eur. J. 2010, 16, 4739;
29. H. A. Wegner, M. Auzias, Angew. Chem. Int. Ed. 2011, 50, 8236;
30. Angew. Chem. 2011, 123, 8386;
31. A. Leyva-Pérez, A. Doménech, S. I. Al-Resayes, A. Corma, ACS Catal. 2012, 2, 121.
32. B. Sahoo, M. N. Hopkinson, F. Glorius, J. Am. Chem. Soc. 2013, 135, 5505;
33. A. Tlahuext-Aca, M. N. Hopkinson, B. Sahoo, F. Glorius, Chem. Sci. 2016, 7, 89;
34. A. Tlahuext-Aca, M. N. Hopkinson, R. A. Garza-Sanchez, F. Glorius, Chem. Eur. J. 2016, 22, 5909;
35. M. N. Hopkinson, A. Tlahuext-Aca, F. Glorius, Acc. Chem. Res. 2016, 49, 2261.
36. W. J. Wolf, M. S. Winston, F. D. Toste, Nat. Chem. 2013, 6, 159;
37. X. Shu, M. Zhang, Y. He, H. Frei, F. D. Toste, J. Am. Chem. Soc. 2014, 136, 5844;
38. S. Kim, J. Rojas-Martin, F. D. Toste, Chem. Sci. 2016, 7, 85;
39. H. Kawai, W. J. Wolf, A. G. DiPasquale, M. S. Winston, F. D. Toste, J. Am. Chem. Soc. 2016, 138, 587.
40. J. Xie, S. Shi, T. Zhang, N. Mehrkens, M. Rudolph, A. S. K. Hashmi, Angew. Chem. Int. Ed. 2015, 54, 6046;
41. Angew. Chem. 2015, 127, 6144;
42. J. Xie, T. Zhang, F. Chen, N. Mehrkens, F. Rominger, M. Rudolph, A. S. K. Hashmi, Angew. Chem. Int. Ed. 2016, 55, 2934;
43. Angew. Chem. 2016, 128, 2987;
44. L. Huang, M. Rudolph, F. Rominger, A. S. K. Hashmi, Angew. Chem. Int. Ed. 2016, 55, 4808;
45. Angew. Chem. 2016, 128, 4888.
46. T. de Haro, C. Nevado, Angew. Chem. Int. Ed. 2011, 50, 906;
47. Angew. Chem. 2011, 123, 936;
48. G. Revol, T. MaCallum, M. Morin, F. Gagosz, L. Barriault, Angew. Chem. Int. Ed. 2013, 52, 13342;
49. Angew. Chem. 2013, 125, 13584;
50. J. H. An, H. Yun, S. Shin, Adv. Synth. Catal. 2014, 356, 3749;
51. D. V. Patil, H. Yun, S. Shin, Adv. Synth. Catal. 2015, 357, 2622;
52. J. Um, H. Yun, S. Shin, Org. Lett. 2016, 18, 484;
53. V. Gauchot, A. Lee, Chem. Commun. 2016, 52, 10163;
54. T. Cornilleau, P. Hermange, E. Fouquet, Chem. Commun. 2016, 52, 10040;
55. B. Alcaide, P. Almendros, E. Busto, A. Luna, Adv. Synth. Catal. 2016, 358, 1526;
56. H. Li, C. Shan, C. Tung, Z. Xu, Chem. Sci. 2017, Advance Article https://doi.org/10.1039/C6SC05093J.
57. For reviews on diazonium salts in cross-couplings, see:
58. S. Bräse, Acc. Chem. Res. 2004, 37, 805;
59. A. Roglans, A. Pla-Quintana, M. Moreno-Mañas, Chem. Rev. 2006, 106, 4622;
60. F. Mo, G. Dong, Y. Zhang, J. Wang, Org. Biomol. Chem. 2013, 11, 1582. For selected examples using diazonium, see:
61. C. Molinaro, J. Mowat, F. Gosselin, P. D. O'Shea, J. F. Marcoux, R. Angelaud, I. W. Davies, J. Org. Chem. 2007, 72, 1856;
62. I. P. Beletskaya, A. S. Sigeev, A. S. Peregudov, P. V. Petrovskii, Synthesis 2007, 2534;
63. G. Danoun, B. Bayarmagnai, M. F. Grünberg, L. J. Gooβen, Angew. Chem. Int. Ed. 2013, 52, 7972;
64. Angew. Chem. 2013, 125, 8130;
65. J. Dai, C. Fang, B. Xiao, J. Yi, J. Xu, Z. Liu, X. Lu, L. Liu, Y. Fu, J. Am. Chem. Soc. 2013, 135, 8436;
66. X. Wang, Y. Xu, F. Mo, G. Ji, D. Qiu, J. Feng, Y. Ye, S. Zhang, Y. Zhang, J. Wang, J. Am. Chem. Soc. 2013, 135, 10330;
67. C. Matheis, L. V. J. Wagner, Chem. Eur. J. 2016, 22, 79;
68. M. Hofer, A. Genoux, R. Kumar, C. Nevado, Angew. Chem. Int. ed. 2017, 56, 1021;
69. Angew. Chem. 2017, 129, 1041.
70. C. Galli, Chem. Rev. 1988, 88, 765;
71. M. R. Heinrich, A. Wetzel, M. Kirschstein, Org. Lett. 2007, 9, 3833;
72. D. P. Hari, B. Kçnig, Angew. Chem. Int. Ed. 2013, 52, 4734;
73. Angew. Chem. 2013, 125, 4832;
74. A. Tlahuext-Aca, M. N. Hopkinson, D. C. G. Glorius, Chem. Eur. J. 2016, 22, 11587.
75. For selected AuIII intermediates, see:
76. J. Guenther, S. Mallet-Ladeira, L. Estevez, K. Miqueu, A. Amgoune, D. Bourissou, J. Am. Chem. Soc. 2014, 136, 1778;
77. M. Livendahl, C. Goehry, F. Maseras, A. Echavarren, Chem. Commun. 2014, 50, 1533;
78. E. O. Asomoza-Solís, J. Rojas-Ocampo, R. A. Toscano, S. Porcel, Chem. Commun. 2016, 52, 7295;
79. L. Huang, F. Rominger, M. Rudolph, A. S. K. Hashmi, Chem. Commun. 2016, 52, 6435;
80. R. Kumar, A. Linden, C. Nevado, J. Am. Chem. Soc. 2016, 138, 13790;
81. J. Serra, T. Parella, X. Ribas, Chem. Sci. 2017, 8, 946;
82. R. Bhattacharjee, A. Nijamudheen, A. Datta, Chem. Eur. J. 2017, 23, 4169.
83. For selected AuI catalyzed alkene difunctionalization, see:
84. C. F. Bender, R. A. Widenhoefer, Org. Lett. 2006, 8, 5303;
85. Z. Zhang, S. D. Lee, R. A. Widenhoefer, J. Am. Chem. Soc. 2009, 131, 5372;
86. M. Chiarucci, M. Bandini, Beilstein J. Org. Chem. 2013, 9, 2586;
87. T. Tamai, K. Fujiwara, S. Higashimae, A. Nomoto, A. Ogawa, Org. Lett. 2016, 18, 2114.
88. For reviews on allene difunctionalization, see:
89. A. Minatti, K. Muňiz, Chem. Soc. Rev. 2007, 36, 1142;
90. E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocomola, Chem. Rev. 2007, 107, 5318;
91. K. H. Jensen, M. S. Sigman, Org. Biomol. Chem. 2008, 6, 4083;
92. R. I. McDonald, G. Liu, S. Stahl, J. Am. Chem. Soc. 2011, 133, 16809;
93. X. Zeng, Chem. Rev. 2013, 113, 6864;
94. S. E. Allen, R. R. Walvoord, R. Padilla-Salinas, M. C. Kozlowski, Chem. Rev. 2013, 113, 6234.
95. M. Hartmann, Y. Li, A. Studer, J. Am. Chem. Soc. 2012, 134, 16516;
96. Z. Xia, Q. Zhu, Org. Lett. 2013, 15, 4110;
97. S. Kindt, K. Wicht, M. R. Heinrich, Org. Lett. 2015, 17, 6122.
98. S. B. Höfling, M. R. Heinrich, Synthesis 2011, 173;
99. G. Pratsch, T. Wallaschkowski, M. R. Heinrich, Chem. Eur. J. 2012, 18, 11555;
100. S. Kindt, K. Wicht, M. R. Heinrich, Angew. Chem. Int. Ed. 2016, 55, 8744.
101. R. Cai, M. Lu, E. Y. Aguilera, Y. Xi, N. G. Akhmedov, J. L. Peterson, H. Chen, X. Shi, Angew. Chem. Int. Ed. 2015, 54, 8772;
102. Angew. Chem. 2015, 127, 8896.
103. H. Peng, R. Cai, C. Xu, H. Chen, X. Shi, Chem. Sci. 2016, 7, 6190.
104. M. S. Winston, W. J. Wolf, F. D. Toste, J. Am. Chem. Soc. 2015, 137, 7921.
105. C. Yang, C. He, J. Am. Chem. Soc. 2005, 127, 6966;
106. L. Coulombel, I. Favier, E. Duñach, Chem. Commun. 2005, 17, 2286.
107. Due to the dimethyl group in 5-position, strong steric effects lead to the kinetically more favorable 6-endo cyclization.
108. For allene functionalization, see:
109. S. Yu, S. Ma, Angew. Chem. Int. Ed. 2012, 51, 3074;
110. Angew. Chem. 2012, 124, 3128;
111. B. Alcaide, P. Almendros, Acc. Chem. Res. 2014, 47, 939;
112. A. S. K. Hashmi, W. Yang, F. Rominger, Adv. Synth. Catal. 2012, 354, 1273;
113. S. Hosseyni, Y. Su, X. Shi, Org. Lett. 2015, 17, 6010;
114. D. V. Vidhani, M. E. Krafft, I. A. Alabugin, J. Am. Chem. Soc. 2016, 138, 2769;
115. T. Jiménez, J. Carreras, J. Ceccon, A. Echavarren, Org. Lett. 2016, 18, 1410.
116. For alkyne functionalization, see:
117. M. C. Willis, Chem. Rev. 2010, 110, 725;
118. J. R. Johansson, T. Beke-Somfai, A. S. Stålsmeden, N. Kann, Chem. Rev. 2016, 116, 14726;
119. C. Bürki, A. Whyte, S. Arndt, A. S. K. Hashmi, M. Lautens, Org. Lett. 2016, 18, 5058;
120. S. Hosseyni, L. Wojtas, M. Li, X. Shi, J. Am. Chem. Soc. 2016, 138, 3994.
121. G. Zhang, Y. Peng, L. Cui, L. Zhang, Angew. Chem. Int. Ed. 2009, 48, 3112.