Platinum-catalyzed synthesis of substituted phenanthrenes from biphenyl propargyl alcohols via a carbene intermediate

Organic Letters

Volumn 16, Issue 18, 2014, Pages 4936-4939

  Kwon, Yongseok ^a   Kim, Illan ^a   Kim, Sanghee ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; ANTOFINE; CARBENE; INDOLE DERIVATIVE; METHANE; PHENANTHRENE DERIVATIVE; PHENANTHROLINE DERIVATIVE; PLATINUM CHLORIDE; PLATINUM DERIVATIVE; PROPANOL; PROPARGYL ALCOHOL;

ANALOGS AND DERIVATIVES; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKYNES; CATALYSIS; CYCLIZATION; INDOLES; METHANE; MOLECULAR STRUCTURE; PHENANTHRENES; PHENANTHROLINES; PLATINUM COMPOUNDS; PROPANOLS;

EID: 84927656413     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502465e     Document Type: Article

References (57)

1. For selected reviews, see: (a) Furstner, A. Chem. Soc. Rev. 2009, 38, 3208.
2. (b) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351.
3. (c) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326.
4. (d) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395.
5. (e) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Commun. 2007, 333.
6. (f) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.
7. (g) Furstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410.
8. For reviews on the transition metal-catalyzed acyloxy migration of propargyl esters, see: (a) Shu, X.-Z.; Shu, D.; Schienebeck, C. M.; Tang, W. Chem. Soc. Rev. 2012, 41, 7698.
9. (b) Xiao, J.; Li, X. Angew. Chem., Int. Ed. 2011, 50, 7226.
10. (c) Wang, S.; Zhang, G; Zhang, L. Synlett 2010, 692.
11. (d) Marion, N; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2750.
12. (e) Marco-Contelles, J.; Soriano, E. Chem.-Eur. J. 2007, 13, 1350.
13. For recent examples of reactions via α, β-unsaturated metal carbene, see: (a) Xia, Y.; Qu, S.; Xiao, Q.; Wang, Z.-X.; Qu, P.; Chen, L.; Liu, Z.; Tian, L.; Huang, Z.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2013, 135, 13502.
14. (b) Sanz, R; Miguel, D.; Gohain, M.; García-García, P.; Fernández-Rodríguez, M. A.; González-Pérez, A.; Nieto-Faza, O.; De Lera, Á. R; Rodríguez, F. Chem.-Eur. J. 2010, 16, 9818.
15. (c) Dudnik, A. S.; Xia, Y.; Li, Y.; Gevorgyan, V. J. Am. Chem. Soc. 2010, 132, 7645.
16. (d) Oh, C. H.; Lee, J. H.; Lee, S. J.; Kim, J. I.; Hong, C. S. Angew. Chem., Int. Ed. 2008, 47, 7505.
17. (e) Zhang, G.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 12598.
18. (f) Lin, G.-Y.; Li, C.-W.; Hung, S.-H; Liu, R.-S. Org. Lett. 2008, 10, 5059.
19. (g) Shapiro, N. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 4160.
20. (h) Peng, L.; Zhang, X.; Zhang, S.; Wang, J. J. Org. Chem. 2007, 72, 1192.
21. For select examples of the heteroatom-based nucleophilic attack and loss of a leaving group, see: (a) Allegretti, P. A.; Ferreira, E. M. J. Am. Chem. Soc. 2013, 135, 17266.
22. (b) Allegretti, P. A.; Ferreira, E. M. Org. Lett. 2011, 13, 5924.
23. (c) Allegretti, P. A.; Ferreira, E. M. Chem. Sci. 2013, 4, 1053.
24. (d) Yang, W.; Wang, T.; Yu, Y.; Shi, S.; Zhang, T.; Hashmi, A. S. K. Adv. Synth. Catal. 2013, 355, 1523.
25. (e) Shu, D.; Song, W.; Li, X.; Tang, W. Angew. Chem., Int. Ed. 2013, 52, 3237.
26. (f) Shu, D.; Winston-McPherson, G N; Song, W.; Tang, W. Org. Lett. 2013, 15, 4162.
27. (g) Saito, K.; Sogou, H; Suga, T.; Kusama, H; Iwasawa, N J. Am. Chem. Soc. 2010, 133, 689.
28. (h) Nakamura, I.; Sato, Y.; Terada, M. J. Am. Chem. Soc. 2009, 131, 4198.
29. (i) Ye, L.; Cui, L.; Zhang, G; Zhang, L. J. Am. Chem. Soc. 2010, 132, 3258.
30. (j) Hiroya, K; Matsumoto, S.; Ashikawa, M.; Ogiwara, K.; Sakamoto, T. Org. Lett. 2006, 8, 5349.
31. (k) Gorin, D. J.; Davis, N. R; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260.
32. For select examples of the carbon-based nucleophilic attack and loss of a leaving group, see: (a) Tsai, F.-Y.; Lo, J.-X.; Hsu, H.-T.; Lin, Y.-C.; Huang, S.-L.; Wang, J.-C.; Liu, Y.-H. Chem.-Asian J. 2013, 8, 2833.
33. (b) Tsai, F.-Y.; Ma, H.-W.; Huang, S.-L.; Lin, Y.-C.; Wang, Y.; Liu, Y.-H. Chem.-Eur. J. 2012, 18, 3399.
34. (c) Chung, C.-P.; Chen, C.-C.; Lin, Y.-C.; Liu, Y.-H.; Wang, Y. J. Am. Chem. Soc. 2009, 131, 18366.
35. (d) Taduri, B. P.; Sohel, S. M. A; Cheng, H.-M.; Lin, G.-Y.; Liu, R.-S. Chem. Commun. 2007, 2530.
36. Kwon, Y.; Cho, H; Kim, S. Org. Lett. 2013, 15, 920.
37. For the Lewis acid-catalyzed Friedel-Crafts cyclization reactions of biaryl alcohols, see: Li, G; Wang, E.; Chen, H; Li, H; Liu, Y.; Wang, P. G Tetrahedron 2008, 64, 9033.
38. For select 1, 2-H shifts of metal carbenes, see: (a) Cho, E. J.; Lee, D. Adv. Synth. Catal. 2008, 350, 2719.
39. (b) Zhang, G; Catalano, V. J.; Zhang, L. J. Am. Chem. Soc. 2007, 129, 11358.
40. (c) Kusama, H; Yamabe, H; Onizawa, Y.; Hoshino, T.; Iwasawa, N. Angew. Chem., Int. Ed. 2005, 44, 468.
41. (d) Taber, D. F.; Herr, R J.; Pack, S. K; Geremia, J. M. J. Org. Chem. 1996, 61, 2908.
42. (e) Ikota, N; Takamura, N; Young, S. D.; Ganem, B. Tetrahedron Lett. 1981, 22, 4163. See also ref 4a and references cited therein.
43. (a) Cambeiro, F.; Lopez, S.; Varela, J. A; Saa, C. Angew. Chem., Int. Ed. 2012, 51, 723.
44. (b) Davies, H. M. L.; Manning, J. R Nature 2008, 451, 417.
45. (c) For a recent review of catalytic carbene insertion into C-H bonds, see: Doyle, M. P.; Duffy, R; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704.
46. (a) Chu, G. M.; Fernandez, I.; Sierra, M. A J. Org. Chem. 2013, 78, 865.
47. (b) Barluenga, J.; De Saa, D.; Gomez, A; Ballesteros, A; Santamaría, J.; De Prado, A.; Tomas, M.; Suarez-Sobrino, A. L. Angew. Chem., Int. Ed. 2008, 47, 6225.
48. (c) Bertani, R; Biasiolo, M.; Darini, K; Mchelin, R A.; Mozzon, M.; Visentin, F.; Zanotto, L. J. Organomet. Chem. 2002, 642, 32.
49. For a recent total synthesis of antofine, see: (a) Yi, M.; Gu, P.; Kang, X.-Y.; Sun, J.; Li, R; Li, X.-Q. Tetrahedron Lett. 2014, 55, 105.
50. (b) Ying, W.; Herndon, J. W. Eur. J. Org. Chem. 2013, 3112.
51. (c) Niphakis, M. J.; Georg, G I. Org. Lett. 2011, 13, 196.
52. (d) Pansare, S. V.; Lingampally, R; Dyapa, R Eur. J. Org. Chem. 2011, 2235.
53. (a) King, F. D. Tetrahedron 2007, 63, 2053.
54. (b) Pichon, M.; Figadere, B.; Cave, A. Tetrahedron Lett. 1996, 37, 7963.
55. Lundkvist, J. RM.; Ringdahl, B.; Hacksell, U. J. Med. Chem. 1989, 32, 863.
56. (a) Lebrun, S.; Couture, A.; Deniau, E.; Grandclaudon, P. Tetrahedron 1999, 55, 2659.
57. (b) Kim, S.; Lee, J.; Lee, T.; Park, H.-g.; Kim, D. Org. Lett. 2003, 5, 2703.