The rich reactivity of transition metal carbenes with alkynes

Tetrahedron Letters

Volumn 57, Issue 35, 2016, Pages 3881-3891

  Torres, Òscar ^a   Pla Quintana, Anna ^a  

^a UNIVERSITY OF GIRONA   (Spain)

Author keywords

Alkyne; Carbene alkyne metathesis; Cyclopropenation; Migratory insertion; Transition metal carbene

Indexed keywords

ALKYNE; CARBENE;

CATALYSIS; CHEMICAL REACTION; CYCLOADDITION; DECOMPOSITION; MICHAEL ADDITION; REACTION ANALYSIS; REVIEW;

EID: 84982703829     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2016.07.029     Document Type: Review

References (87)

1. 1(a) For selected reviews, see:Davies, H.M.L., Manning, J.R., Nature 451 (2008), 417–424.
2. 1(b) Padwa, A., Chem. Soc. Rev. 38 (2009), 3072–3081.
3. 1(c) Doyle, M.P., Duffy, R., Ratnikov, M., Zhou, L., Chem. Rev. 110 (2010), 704–724.
4. 1(d) Zhao, X., Zhang, Y., Wang, J., Chem. Commun., 2012, 10162–10173.
5. 1(e) Xiao, Q., Zhang, Y., Wang, J., Acc. Chem. Res. 46 (2013), 236–247.
6. 1(f) Gillingham, D., Fei, N., Chem. Soc. Rev., 42, 2013, 4918.
7. 1(g) Ford, A., Miel, H., Ring, A., Slattery, C.N., Maguire, A.R., McKervey, M.A., Chem. Rev. 115 (2015), 9981–10080.
8. 2(a) Jones, V.K., Deutschman, A.J. Jr., J. Org. Chem. 30 (1965), 3978–3980.
9. 2(b) Vidal, M., Vincens, M., Arnaud, P., Bull. Soc. Chim. Fr., 1972, 657–665.
10. 2(c) Dolgii, I.E., Shapiro, E.A., Nefedov, O.M., Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.), 23, 1974 929–929.
11. 2(d) Shapiro, E.A., Dolgii, I.E., Nefedov, O.M., Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 29 (1980), 1493–1499.
12. 2(e) Baikov, V.E., Danilkina, L.P., Ogloblin, K.A., Russ. J. Gen. Chem. 53 (1983), 2172–2173.
13. 3 Suárez, A., Fu, G.C., Angew. Chem., Int. Ed. 43 (2004), 3580–3582.
14. 4 Hassink, M., Liu, X., Fox, J.M., Org. Lett. 13 (2011), 2388–2391.
15. 5(a) Zhou, L., Ma, J., Zhang, Y., Wang, J., Tetrahedron Lett. 52 (2011), 5484–5487.
16. 5(b) Zhou, L., Ma, J., Zhang, Y., Wang, J., Tetrahedron Lett., 54, 2013 2558–2558.
17. 6 Xiao, Q., Xia, Y., Li, H., Zhang, Y., Wang, J., Angew. Chem., Int. Ed. 50 (2011), 1114–1117.
18. 7 Hossain, M.L., Ye, F., Zhang, Y., Wang, J., J. Org. Chem. 78 (2013), 1236–1241.
19. 8 Wu, C., Hu, F., Liu, Z., Deng, G., Ye, F., Zhang, Y., Wang, J., Tetrahedron 71 (2015), 9196–9201.
20. 9 Ye, F., Wang, C., Ma, X., Hossain, M.L., Xia, Y., Zhang, Y., Wang, J., J. Org. Chem. 80 (2015), 647–652.
21. 10 Ye, F., Ma, X., Xiao, Q., Li, H., Zhang, Y., Wang, J., J. Am. Chem. Soc. 134 (2012), 5742–5745.
22. 11 Li, J., Ding, D., Liu, L., Sun, J., RSC Adv. 3 (2013), 21260–21266.
23. 12 Xiao, T., Zhang, P., Xie, Y., Wang, J., Zhou, L., Org. Biomol. Chem. 12 (2014), 6215–6222.
24. 13 Poh, J.-S., Tran, D.N., Battilocchio, C., Hawkins, J.M., Ley, S.V., Angew. Chem., Int. Ed. 54 (2015), 7920–7923.
25. 14 Tang, Y., Chen, Q., Liu, X., Wang, G., Lin, L., Feng, X., Angew. Chem., Int. Ed. 54 (2015), 9512–9516.
26. 15 Wang, T., Wang, M., Fang, S., Liu, J.-Y., Organometallics 33 (2014), 3941–3949.
27. 16 Zhou, L., Ye, F., Ma, J., Zhang, Y., Wang, J., Angew. Chem., Int. Ed. 50 (2011), 3510–3514.
28. 17 Zhang, Z., Zhou, Q., Yu, W., Li, T., Wu, G., Zhang, Y., Wang, J., Org. Lett. 17 (2015), 2474–2477.
29. 18 Liu, H., Feng, W., Kee, C.W., Leow, D., Loh, W.-T., Tan, C.-H., Adv. Synth. Catal. 352 (2010), 3373–3379.
30. 19 Zhou, L., Shi, Y., Xiao, Q., Liu, Y., Ye, F., Zhang, Y., Wang, J., Org. Lett. 13 (2011), 968–971.
31. 20 Kumaraswamy, G., Jayaprakash, N., Balakishan, G., Org. Biomol. Chem. 9 (2011), 7913–7920.
32. 21 Ye, F., Shi, Y., Zhou, L., Xiao, Q., Zhang, Y., Wang, J., Org. Lett. 13 (2011), 5020–5023.
33. 22 Mondal, S., Nechab, M., Campolo, D., Vanthuyne, N., Bertrand, M.P., Adv. Synth. Catal. 354 (2012), 1987–2000.
34. 23 Liu, G., Xu, G., Li, J., Ding, D., Sun, J., Org. Biomol. Chem. 12 (2014), 1387–1390.
35. 24 Kumaraswamy, G., Balakishan, G., Eur. J. Org. Chem., 2015, 3141–3146.
36. 25 Liu, K., Zhu, C., Min, J., Peng, S., Xu, G., Sun, J., Angew. Chem., Int. Ed. 54 (2015), 12962–12967.
37. 26 Paul, N.D., Mandal, S., Otte, M., Cui, X., Zhang, X.P., de Bruin, B., J. Am. Chem. Soc. 136 (2014), 1090–1096.
38. 27 Helan, V., Gulevich, A.V., Gevorgyan, V., Chem. Sci. 6 (2015), 1928–1931.
39. 28 Zhou, L., Ye, F., Zhang, Y., Wang, J., J. Am. Chem. Soc. 132 (2010), 13590–13591.
40. 29 Wang, C., Ye, F., Wu, C., Zhang, Y., Wang, J., J. Org. Chem. 80 (2015), 8748–8757.
41. 30 Ye, F., Hossain, M.L., Xu, Y., Ma, X., Xiao, Q., Zhang, Y., Wang, J., Chem. Asian J. 8 (2013), 1404–1407.
42. 31 Wang, N.-N., Huang, L.-R., Hao, W.-J., Zhang, T.-S., Li, G., Tu, S.-J., Jiang, B., Org. Lett. 18 (2016), 1298–1301.
43. 32 Zhou, Y., Ye, F., Zhou, Q., Zhang, Y., Wang, J., Org. Lett. 18 (2016), 2024–2027.
44. 33 Chen, Z.-S., Duan, X.-H., Zhou, P.-X., Ali, S., Luo, J.-Y., Liang, Y.-M., Angew. Chem., Int. Ed. 51 (2012), 1370–1374.
45. 34 Xia, J., Feng, S., Liu, Z., Zhang, Y., Wang, J., Angew. Chem., Int. Ed. 54 (2015), 7891–7894.
46. 35(a) Marek, I., Simaan, S., Masarwa, A., Angew. Chem., Int. Ed. 46 (2007), 7364–7376.
47. 35(b) Zhu, Z.-B., Wei, Y., Shi, M., Chem. Soc. Rev. 40 (2011), 5534–5563.
48. 36 Uehara, M., Suematsu, H., Yasutomi, Y., Katsuki, T., J. Am. Chem. Soc. 133 (2011), 170–171.
49. 37 Cui, X., Xu, X., Lu, H., Zhu, S., Wojtas, L., Zhang, X.P., J. Am. Chem. Soc. 133 (2011), 3304–3307.
50. 38 Lindsay, V.N.G., Fiset, D., Gritsch, P.J., Azzi, S., Charette, A.B., J. Am. Chem. Soc. 135 (2013), 1463–1470.
51. 39 Goto, T., Takeda, K., Shimada, N., Nambu, H., Anada, M., Shiro, M., Ando, K., Hashimoto, S., Angew. Chem., Int. Ed. 50 (2011), 6803–6808.
52. 40 Gong, J., Zhao, Z., Zhang, F., Wu, S., Yan, G., Quan, Y., Ma, B., Org. Lett. 16 (2014), 5524–5527.
53. 41 Briones, J.F., Davies, H.M.L., Tetrahedron 67 (2011), 4313–4317.
54. 42 Briones, J.F., Davies, H.M.L., Org. Lett. 13 (2011), 3984–3987.
55. 43 Briones, J.F., Davies, H.M.L., J. Am. Chem. Soc. 134 (2012), 11916–11919.
56. 44 Swenson, A.K., Higgins, K.E., Brewer, M.G., Brennessel, W.W., Coleman, M.G., Org. Biomol. Chem. 10 (2012), 7483–7486.
57. 45 Thomas, T.J., Merritt, B.A., Lemma, B.E., McKoy, A.M., Nguyen, T., Swenson, A.K., Mills, J.L., Coleman, M.G., Org. Biomol. Chem. 14 (2016), 1742–1747.
58. 46 Edwards, A., Rubin, M., Tetrahedron 71 (2015), 3237–3246.
59. 47 Gulevich, A.V., Dudnik, A.S., Chernyak, N., Gevorgyan, V., Chem. Rev. 113 (2013), 3084–3213.
60. 48 Cui, X., Xu, X., Wojtas, L., Kim, M.M., Zhang, X.P., J. Am. Chem. Soc. 134 (2012), 19981–19984.
61. 49 Xia, L., Lee, Y.R., Eur. J. Org. Chem., 2014, 3430–3442.
62. 50 Hossain, M.L., Ye, J., Zhang, Y., Wang, J., Tetrahedron 70 (2014), 6957–6962.
63. 51 Kurandina, D., Gevorgyan, V., Org. Lett. 18 (2016), 1804–1807.
64. 52(a) Padwa, A., Weingarten, M.D., Chem. Rev. 96 (1996), 223–269.
65. 52(b) Padwa, A., J. Organomet. Chem. 610 (2000), 88–101.
66. 53 Qian, Y., Shanahan, C.S., Doyle, M.P., Eur. J. Org. Chem., 2013, 6032–6037.
67. 54(a) Jansone-Popova, S., May, J.A., J. Am. Chem. Soc. 134 (2012), 17877–17880.
68. 54(b) Jansone-Popova, S., Le, P.Q., May, J.A., Tetrahedron 70 (2014), 4118–4127.
69. 55 Le, P.Q., May, J.A., J. Am. Chem. Soc. 137 (2015), 12219–12222.
70. 56 Shi, Y., Gevorgyan, V., Org. Lett. 15 (2013), 5394–5396.
71. 57 Zheng, Y., Mao, J., Weng, Y., Zhang, X., Xu, X., Org. Lett. 17 (2015), 5638–5641.
72. 58 Yao, R., Rong, G., Yan, B., Qiu, L., Xu, X., ACS Catal. 6 (2016), 1024–1027.
73. 59 Torres, Ò., Parella, T., Solà, M., Roglans, A., Pla-Quintana, A., Chem. Eur. J. 21 (2015), 16240–16245.
74. 60 Wang, X., Zhou, Y., Qiu, L., Yao, R., Zheng, Y., Zhang, C., Bao, X., Xu, X., Adv. Synth. Catal. 358 (2016), 1571–1576.
75. 61(a) Le Paih, J., Dérien, S., Özdemir, I., Dixneuf, P.H., J. Am. Chem. Soc. 122 (2000), 7400–7401.
76. 61(b) Vovard-Le Bray, C., Dérien, S., Dixneuf, P.H., Angew. Chem., Int. Ed. 48 (2009), 1439–1442.
77. 61(c) Moulin, S., Zhang, H., Raju, S., Bruneau, C., Dérien, S., Chem. Eur. J. 19 (2013), 3292–3296.
78. 62(a) Monnier, F., Castillo, D., Dérien, S., Toupet, L., Dixneuf, P.H., Angew. Chem., Int. Ed. 42 (2003), 5474–5477.
79. 62(b) Monnier, F., Vovard-Le Bray, C., Castillo, D., Aubert, V., Dérien, S., Dixneuf, P.H., Toupet, L., Ienco, A., Mealli, C., J. Am. Chem. Soc. 129 (2007), 6037–6049.
80. 62(c) Eckert, M., Monnier, F., Shchetnikov, G.T., Titanyuk, I.D., Osipov, S.N., Toupet, L., Dérien, S., Dixneuf, P.H., Org. Lett. 17 (2005), 3741–3743.
81. 63 Vovard-Le Bray, C., Dérien, S., Dixneuf, P.F., Murakami, M., Synlett, 2008, 193–196.
82. 64(a) Ni, Y., Montgomery, J., J. Am. Chem. Soc. 126 (2004), 11162–11163.
83. 64(b) Ni, Y., Montgomery, J., J. Am. Chem. Soc. 128 (2006), 2609–2614.
84. 65 Panne, P., Fox, J.M., J. Am. Chem. Soc. 129 (2007), 22–23.
85. 66(a) Cambeiro, F., López, S., Varela, J.A., Saá, C., Angew. Chem., Int. Ed. 51 (2012), 723–727.
86. 66(b) Cambeiro, F., López, S., Varela, J.A., Saá, C., Angew. Chem., Int. Ed. 53 (2014), 5959–5963.
87. 66(c) González-Rodríguez, C., Suárez, J.R., Varela, J.A., Saá, C., Angew. Chem., Int. Ed. 54 (2015), 2724–2728.