A highly active and general catalyst for the stille coupling reaction of unreactive aryl, heteroaryl, and vinyl chlorides under mild conditions

Advanced Synthesis and Catalysis

Volumn 355, Issue 9, 2013, Pages 1729-1735

  Lee, Dong Hwan ^a   Qian, Yingjie ^a   Park, Ji Hoon ^a   Lee, Jong Suk ^a   Shim, Sang Eun ^a   Jin, Myung Jong ^a  

^a Inha University   (South Korea)

Author keywords

aryl chlorides; C C coupling; homogeneous catalysis; palladium; Stille reaction

Indexed keywords

EID: 84879199780     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201300075     Document Type: Article

References (60)

1. For reviews, see; a) J. K. Stille, Pure Appl. Chem. 1985, 57, 1771;
2. b) M. Pereyre, J. P. Quintard, A. Rahm, Tin in Organic Synthesis Butterworth, London 1987;
3. c)V. Farina, V. Krishnamurthy, W. J. Scott, The Stille Reaction, John Wiley & Sons, New York, 1998;
4. d)T.N. Mitchell, Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, 2004;
5. e) P. Espinet, A. M. Echavarren, Angew. Chem. 2004, 116, 4808;
6. Angew. Chem. Int. Ed. 2004, 43, 4704;
7. f) C. Valente, S. Calimsiz, K. H. Hoi, D. Mallik, M. Sayah, M. G. Organ, Angew. Chem. 2012, 124, 3370;
8. Angew. Chem. Int. Ed. 2012, 51, 3314.
9. a) G. Bringmann, D. Menche, Acc. Chem. Res. 2001, 34, 615;
10. b) G. Bringmann, Y. Reichert, V. V. Kane, Tetrahedron 2004, 60, 3539;
11. c) T. W. Wallace, Org. Biomol. Chem. 2006, 4, 3197;
12. d) T. C. Roberts, P. A. Smith, R. T. Cirz, R. E. Romesberg, J. Am. Chem. Soc. 2007, 129, 15830;
13. e) W. Yue, A. Lv, J. Gao, W. Jiang, L. Hao, C. Li, Y. Li, L. E. Polander, S. Barlow, W. Hu, S. D. Motta, F. Negri, S. R. Marder, Z. Wang, J. Am. Chem. Soc. 2012, 134, 5770.
14. a) W.-S. Kim, H.-J. Kim, C.-G. Cho, Tetrahedron Lett. 2002, 43, 9015;
15. b) S. P. H. Mee, V. Lee, J. E. Baldwin, Angew. Chem. 2004, 116, 1152;
16. Angew. Chem. Int. Ed. 2004, 43, 1132;
17. c) D. Olsson, P. Nilsson, M. E. Masnaouy, O. F. Wendt, Dalton Trans. 2005, 1924;
18. d) J.-H. Li, Y. Liang, D.-P. Wang, W.-J. Liu, Y.-X. Xie, D.-L. Yin, J. Org. Chem. 2005, 70, 2832;
19. e) S. P. H. Mee, V. Lee, J. E. Baldwin, Chem. Eur. J. 2005, 11, 3294;
20. f) W. Shi, C. Liu, Z. Yu, A. Lei, Chem. Commun. 2007, 2342;
21. g) J. Hämmerle, M. Schnórch, P. Stanetty, Synlett 2007, 2975;
22. h) W.-J. Zhou, K.-H. Wang, J.-X. Wang, Adv. Synth. Catal. 2009, 351, 1378;
23. i) G. Kerric, E. L. Grognec, F. Zammattio, M. Paris, J.-P. Quintard, J. Orgnomet. Chem. 2010, 695, 103;
24. j) Y. Yabe, T. Maegawa, Y. Monguchi, H. Sajiki, Tetrahedron 2010, 66, 8654;
25. k) R. Chotima, T. Dale, M. Green, T. W. Hey, C. L. McMullin, A. Nunns, A. G. Orpen, I. V. Shishkov, D. F. Wass, R. L. Wingad, Dalton Trans. 2011, 40, 5316;
26. l) A. Pal, R. Ghosh, N. N. Adarsh, A. Sarkar, Tetrahedron 2010, 66, 5451;
27. m) J. Sävmarker, J. Lindh, P. Nilsson, Tetrahedron Lett. 2010, 51, 6886;
28. n) E. Flçistrup, P. Goede, R. Strçmberg, J. Malm, Tetrahedron Lett. 2011, 52, 209;
29. o) H. Germain, C. S. Harris, H. Lebraud, Tetrahedron Lett. 2011, 52, 6376;
30. p) L. E. Polander, A. S. Romanov, S. Barlow, D. K. Hwang, B. Kippelen, T. V. Timofeeva, S. R. Marder, Org. Lett. 2012, 14, 918.
31. a) A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350;
32. Angew. Chem. Int. Ed. 2002, 41, 4176;
33. b) A. F. Littke, L. Schwarz, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 6343;
34. c) C. Wolf, R. Lerebours, J. Org. Chem. 2003, 68, 7551;
35. d) R. B. Bedford, C. S. J. Cazin, D. Holder, Coord. Chem. Rev. 2004, 248, 2283.
36. V. V. Grushin, H. Alper, Activation of Unreactive Bonds and Organic Synthesis, Springer, Berlin, 1999.
37. a) A. F. Littke, L. Schwarz, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 6343;
38. b) W. Su, S. Urgaonkar, A. P. McLaughlin, G. Verkade, J. Am. Chem. Soc. 2004, 126, 16433;
39. c) J. R. Naber, S. L. Buchwald, Adv. Synth. Catal. 2008, 350, 957;
40. d) M.-J. Jin, D.-H. Lee, Angew. Chem. 2010, 122, 1137;
41. Angew. Chem. Int. Ed. 2010, 49, 1119;
42. e) D.-H. Lee, A. Taher, W.-S. Ahn, M.-J. Jin, Chem. Commun. 2010, 46, 478;
43. f) M. Dowlut, D. Mallik, M. G. Organ, Chem. Eur. J. 2010, 16, 4279;
44. g) G. Ma, Y. Leng, Y. Wu, Y. Wu, Tetrahedron 2013, 69, 902;
45. h) G.-p. Lu, C. Caib, B. H. Lipshutz, Green Chem. 2013, 15, 105.
46. a) D.-H. Lee, J.-Y. Jung, M.-J. Jin, Chem. Commun. 2010, 46, 9046;
47. b) D.-H. Lee, M.-J. Jin, Org. Lett. 2011, 13, 252;
48. c) D.-H. Lee, A. Taher, S. Hossain, M.-J. Jin, Org. Lett. 2011, 13, 5540;
49. d) D.-H. Lee, M.-J. Jin, Adv. Synth. Catal. 2011, 353, 3090.
50. F. T. Ladipo, G. K. Anderson, Organometallics 1994, 13, 303.
51. a) S.-L. Ku, X.-P. Hui, C.-A. Chen, Y.-Y. Kuo, H.-M. Gau, Chem. Commun. 2007, 3847;
52. b) G. C. Fu, Acc. Chem. Res. Acc. Chem. Res 2008, 41, 1555.
53. a) A. F. Pozharskii, A. T. Spldartenko, A. Katritzky, Heterocycles in Life and Society, Wiley, New York, 1997;
54. b) E. Tyrell, P. Brookes, Synthesis 2004, 469.
55. I. J. S. Fairlamb, Chem. Soc. Rev. Chem. Soc. Rev 2007, 36, 1036.
56. R. N. Hanson, E. McCaskill, P. Tongcharoensirikul, R. Dilis, D. Labaree, R. B. Hochberg, Steroids 2012, 77, 471.
57. J. He, J. L. Crase, S. H. Wadumethrige, K. Thakur, L. Dai, S. Zou, R. Rathore, C. S. Hartley, J. Am. Chem. Soc. 2010, 132, 13848.
58. H. Urabe, K. Suzuki, F. Sato, J. Am. Chem. Soc. 1997, 119, 10014.
59. Y. Li, Z. Qi, H. Wang, X. Fu, C. Duan, J. Org. Chem. 2012, 77, 2053.
60. J. Pan, X. Wang, Y. Zhang, S. L. Buchwald, Org. Lett. 2011, 13, 4974.