Zinc reagents as non-noble catalysts for alkyne activation

Tetrahedron Letters

Volumn 56, Issue 13, 2015, Pages 1600-1608

  González, María J ^a   López, Luis A ^a   Vicente, Rubén ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Alkynes; Catalysis; Zinc

Indexed keywords

ALCOHOL DERIVATIVE; ALKYNE; CARBENE; FUNCTIONAL GROUP; HALIDE; HYDROGEN; INDOLE DERIVATIVE; NITROGEN; OXYGEN; PYRROLE DERIVATIVE; REAGENT; SILICON; TRANSITION ELEMENT; ZINC COMPLEX; ZINC DERIVATIVE;

ACIDITY; ADDITION REACTION; AMINATION; CATALYSIS; CATALYST; CHIRALITY; COVALENT BOND; CYCLIZATION; CYCLOADDITION; DESILYLATION; DIELS ALDER REACTION; ENANTIOSELECTIVITY; HIGH TEMPERATURE; IMMOBILIZATION; MICROWAVE RADIATION; NUCLEOPHILICITY; OLEFINATION; OXIDATION; PROTON TRANSPORT; REACTION TIME; REVIEW; RING OPENING; SILYLATION; SIMMONS SMITH REACTION; SYNTHESIS;

EID: 84924274368     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2015.02.040     Document Type: Review

References (89)

1. F. Diederich, P.J. Stang, and R.R. Tykwinski Acetylene Chemistry 2005 Wiley-VCH Weinheim
2. For reviews on zinc catalysis in organic synthesis, see: (a) X.-F. Wu, and H. Neumann Adv. Synth. Catal. 354 2012 3141
3. X.-F. Wu Chem. Asian J. 7 2012 2502
4. S. Enthaler ACS Catal. 3 2013 150
5. For an account of this transformation, see: D.E. Frantz, R. Fässler, C.S. Tomooka, and E.M. Carreira Acc. Chem. Res. 33 2000 373
6. Selected examples: (a) D.E. Frantz, R. Fässler, and E.M. Carreira J. Am. Chem. Soc. 121 1999 11245
7. R. Fässler, D.E. Frantz, J. Oetiker, and E.M. Carreira Angew. Chem., Int. Ed. 41 2002 3054
8. S. Pinet, S.U. Pandya, P.Y. Chavant, A. Ayling, and Y. Vallee Org. Lett. 4 2002 1463
9. S.K. Patel, S. Py, S.U. Pandya, P.Y. Chavant, and Y. Vallée Tetrahedron: Asymmetry 14 2003 525
10. B. Jiang, Z. Chen, and X. Tang Org. Lett. 4 2002 3451
11. D. Boyall, F. López, H. Sasaki, D. Frantz, and E.M. Carreira Org. Lett. 2 2000 4233
12. N.K. Anand, and E.M. Carreira J. Am. Chem. Soc. 123 2001 9687
13. R. Fässler, C.S. Tomooka, D.E. Frantz, and E.M. Carreira PNAS 101 2004 5843
14. C.W. Downey, B.D. Mahoney, and V.R. Lipari J. Org. Chem. 74 2009 2904
15. T.F. Knöpfel, D. Boyall, and E.M. Carreira Org. Lett. 6 2004 2281
16. S. Reber, T.F. Knöpfel, and E.M. Carreira Tetrahedron 59 2003 6813
17. N. Chinkov, A. Warm, and E.M. Carreira Angew. Chem., Int. Ed. 50 2011 2957
18. E. Ramu, R. Varala, N. Sreelatha, and S.R. Adapa Tetrahedron Lett. 48 2007 7184
19. M.L. Kantam, V. Balasubrahmanyam, K.B.S. Kumar, and G.T. Venkanna Tetrahedron Lett. 48 2007 7332
20. I. Suzuki, M. Yasuda, and A. Baba Chem. Commun. 2013 11620
21. R.J. Rahaim Jr, and J.T. Shaw J. Org. Chem. 73 2008 2912
22. T. Tsuchimoto, M. Fujii, Y. Iketani, and M. Sekine Adv. Synth. Catal. 354 2012 2959
23. K. Kiyokawa, N. Tachikake, M. Yasuda, and A. Baba Angew. Chem., Int. Ed. 50 2011 10393
24. For a review on hydroamination reactions, see: T.E. Müller, K.C. Hultzsch, M. Yus, F. Foubelo, and M. Tada Chem. Rev. 108 2008 3795
25. For early studies on zinc-catalyzed hydroaminations of alkynes, see: (a) R.-Q. Su, and T.E. Müller Tetrahedron 57 2001 6027
26. T.E. Müller, M. Grosche, E. Herdtweck, A.-K. Pleier, E. Walter, and Y.-K. Yan Organometallics 19 2000 170
27. V. Neff, T.E. Müller, and J.A. Lercher Chem. Commun. 2002 906
28. A. Zulys, M. Dochnahl, D. Hollmann, K. Löhnwitz, J.-S. Herrmann, P.W. Roesky, and S. Blechert Angew. Chem., Int. Ed. 44 2005 7794
29. M. Dochnahl, J.-W. Pissarek, S. Blechert, K. Löhnwitz, and P.W. Roesky Chem. Commun. 2006 3405
30. N. Meyer, K. Löhnwitz, A. Zulys, P.W. Roesky, M. Dochnahl, and S. Blechert Organometallics 25 2006 3730
31. For a review on this type of zinc complexes, see: (c) J. Jenter, A. Lühl, P.W. Roesky, and S. Blechert J. Organomet. Chem. 696 2011 406
32. C.T. Duncan, S. Fliisch, and T. Asefa ChemCatChem 1 2009 365
33. C. Duncan, A.V. Biradar, and T. Asefa ACS Catal. 1 2011 736
34. A. Mukherjee, T.K. Sen, P.K. Ghorai, P.P. Samuel, C. Schulzke, and S.K. Mandal Chem. Eur. J. 18 2012 10530
35. A. Lühl, H.-P. Nayek, S. Blechert, and P.W. Roesky Chem. Commun. 2011 8280
36. A. Lühl, L. Hartenstein, S. Blechert, and P.W. Roesky Organometallics 31 2012 7109
37. J.-W. Pissarek, D. Schlesiger, P.W. Roesky, and S. Blechert Adv. Synth. Catal. 351 2009 2081
38. K. Alex, A. Tillack, N. Schwarz, and M. Beller ChemSusChem 1 2008 333
39. See also: (b) T. Tsuchimoto, K. Aoki, T. Wagatsuma, and Y. Suzuki Eur. J. Org. Chem. 2008 4035
40. Y. Yin, W. Ma, Z. Chai, and G. Zhao J. Org. Chem. 72 2007 5731
41. See also: (b) M. Nakamura, L. Ilies, S. Otsubo, and E. Nakamura Angew. Chem., Int. Ed. 45 2006 944
42. K. Okuma, J. Seto, K. Sakaguchi, S. Ozaki, N. Nagahora, and K. Shioji Tetrahedron Lett. 50 2009 2943
43. K. Alex, A. Tillack, N. Schwarz, and M. Beller Angew. Chem., Int. Ed. 47 2008 2304
44. M.P. Kumar, and R.-S. Liu J. Org. Chem. 71 2006 4951
45. K. Alex, A. Tillack, N. Schwarz, and M. Beller Org. Lett. 10 2008 2377
46. For a related zinc-mediated hydroamination using 1,3-enynes, see: (b) N.T. Patil, and V. Singh Chem. Commun. 2011 11116
47. X.-T. Liu, L. Hao, M. Lin, L. Chen, and Z.-P. Zhan Org. Biomol. Chem. 8 2010 3064
48. A.M. Prior, and R.S. Robinson Tetrahedron Lett. 49 2008 411
49. A. Pews-Davtyan, and M. Beller Chem. Commun. 2011 2152
50. M. Biyikal, M. Porta, P.W. Roesky, and S. Blechert Adv. Synth. Catal. 2010 1870 352
51. N. Purkait, and S. Blechert Adv. Synth. Catal. 354 2012 2079
52. P. Wyrebek, A. Sniady, N. Bewick, Y. Li, A. Mikus, K.A. Wheeler, and R. Dembinski Tetrahedron 65 2009 1268
53. S. He, L. Chen, Y.-N. Niu, L.-Y. Wu, and Y.-M. Liang Tetrahedron Lett. 50 2009 2443
54. C.D. Smith, and M.F. Greaney Org. Lett. 15 2013 4826
55. M. Nakamura, L. Ilies, S. Otsubo, and E. Nakamura Org. Lett. 8 2006 2803
56. For a review, see: (b) H. Tsuji, L. Ilies, and E. Nakamura Synlett 2014 2099
57. P. Aschwanden, D.E. Frantz, and E.M. Carreira Org. Lett. 2 2000 2331
58. A. Sniady, A. Durham, M.S. Morreale, K.A. Wheeler, and R. Dembinski Org. Lett. 9 2007 1175
59. A. Sniady, A. Durham, M.S. Morreale, A. Marcinek, S. Szafert, T. Lis, K.R. Brzezinska, T. Iwasaki, T. Ohshima, K. Mashima, and R. Dembinski J. Org. Chem. 73 2008 5881
60. M.H. Al-huniti, and S.D. Lepore Org. Lett. 16 2014 4154
61. M. Nakamura, C. Liang, and E. Nakamura Org. Lett. 2004 2015 6
62. S. Morikawa, S. Yamazaki, M. Tsukada, S. Izuhara, T. Morimoto, and K. Kakiuchi J. Org. Chem. 72 2007 6459
63. S. Yamazaki, S. Morikawa, K. Miyazaki, M. Takebayashi, Y. Yamamoto, T. Morimoto, K. Kakiuchi, and Y. Mikata Org. Lett. 11 2009 2796
64. C.-L. Deng, R.-J. Song, Y.-L. Liu, and J.-H. Li Adv. Synth. Catal. 351 2009 3096
65. W. Hess, and J.W. Burton Adv. Synth. Catal. 353 2011 2966
66. Y. Han, L. Zhu, Y. Gao, and C.-S. Lee Org. Lett. 13 2011 588
67. H.K. Grover, T.P. Lebold, and M.A. Kerr Org. Lett. 13 2011 220
68. T.P. Lebold, A.B. Leduc, and M.A. Kerr Org. Lett. 11 2009 3770
69. K. Endo, T. Hatakeyama, M. Nakamura, and E. Nakamura J. Am. Chem. Soc. 129 2007 5264
70. M. Nakamura, T. Fujimoto, K. Endo, and E. Nakamura Org. Lett. 6 2004 4837
71. For the addition of phenols to propiolates, see: R.A.C. Leão, de F.P. de Moraes, M.C.B.C. Pedro, and P.R.R. Costa Synthesis 2011 3692
72. M.-Y. Lin, A. Das, and R.-S. Liu J. Am. Chem. Soc. 128 2006 9340
73. J.-M. Tang, S. Bhunia, S.M.A. Sohel, M.-Y. Lin, H.-Y. Liao, S. Datta, A. Das, and R.-S. Liu J. Am. Chem. Soc. 129 2007 15677
74. J. Kuang, and S. Ma J. Am. Chem. Soc. 132 2010 1786
75. J. Ye, S. Li, B. Chen, W. Fan, J. Kuang, J. Liu, Y. Liu, B. Miao, B. Wan, Y. Wang, X. Xie, Q. Yu, W. Yuan, and S. Ma Org. Lett. 14 2012 1346
76. M. Periasamy, N. Sanjeevakmar, M. Dalai, R. Gurugrahamam, and P.O. Reddy Org. Lett. 15 2012 2932
77. R. Lü, J. Ye, T. Cao, C. Chen, W. Fan, W. Lin, J. Liu, H. Luo, B. Miao, S. Ni, X. Tang, N. Wang, Y. Wang, X. Xie, Q. Yu, W. Yuan, W. Zhang, C. Zhu, and S. Ma Org. Lett. 15 2013 2254
78. M. Periasamy, P.O. Reddy, and N. Sanjeevakumar Eur. J. Org. Chem. 2013 3866
79. M. Periasamy, P.O. Reddy, A. Edukonladu, M. Dalai, L.M. Alakonda, and B. Udaykumar Eur. J. Org. Chem. 2014 6067
80. T. Sugiishi, and H. Nakamura J. Am. Chem. Soc. 134 2012 2504
81. X. Zhao, X.-G. Zhang, R.-Y. Tang, C.-L. Deng, and J.-H. Li Eur. J. Org. Chem. 2010 4211
82. X.-L. Fang, R.-Y. Tang, X.-G. Zhang, P. Zhong, C.-L. Deng, and J.-H. Li J. Organomet. Chem. 696 2011 352
83. R. Vicente, J. González, L. Riesgo, J. González, and L.A. López Angew. Chem., Int. Ed. 51 2012 8063
84. M.J. González, L.A. López, and R. Vicente Org. Lett. 16 2014 5780
85. B. Song, L.-H. Li, X.-R. Song, Y.-F. Qiu, M.-J. Zhong, P.-X. Zhou, and Y.-M. Liang Chem. Eur. J. 20 2014 5919
86. J. González, L.A. López, and R. Vicente Chem. Commun. 2014 8536
87. J. González, J. González, C. Pérez-Calleja, L.A. López, and R. Vicente Angew. Chem., Int. Ed. 52 2013 5853
88. A.M. Cook, and C. Wolf Chem. Commun. 2014 3151
89. S.A. Gawade, D.B. Huple, and R.-S. Liu J. Am. Chem. Soc. 136 2014 2978