Ligand effects on the Pd-Catalyzed cross-coupling reaction of 3-Iodoalk-2-enoates with Propargyl/1,2-Allenylie metallic species: An efficient regiodivergent synthesis of 2,4,5-Trienoates

Chemistry - A European Journal

Volumn 16, Issue 1, 2010, Pages 74-80

  Zhao, Jinbo ^a   Yu, Yihua ^b   Ma, Shengming ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

Alienes; Cross coupling; Ligand effects; Palladium; Regioselectivity

Indexed keywords

ALIENES; ALLENYL; CHEMICAL EQUATIONS; CROSS COUPLING REACTIONS; CROSS-COUPLINGS; LIGAND EFFECT; LIGAND EFFECTS; METALLIC SPECIES; NEGISHI COUPLING; REGIO-SELECTIVE; TRANSMETALATION;

CHEMICAL BONDS; COMPLEXATION; LIGANDS; LITHIUM; PALLADIUM; REGIOSELECTIVITY; SYNTHESIS (CHEMICAL);

CHELATION;

EID: 73949091413     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901287     Document Type: Article

References (53)

1. For reviews and some selected examples, see: a) Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998;
2. b) Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis (Ed.: J. Tsuji), Wiley, New York, 2003;
3. c) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457;
4. d) J.-P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651;
5. e) E. Negishi, Acc. Chem. Res. 1982, 15, 340;
6. f) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314;
7. g) C. E. Tucker, P. Knochel, J. Org. Chem. 1993, 58, 4781;
8. h) P. Knochel, R. D. Singer, Chem. Rev. 1993, 93, 2117;
9. i) R. Giovannini, P. Knochel, J. Am. Chem. Soc. 1998, 120, 11186;
10. j) T. J. Kom, M. A. Schade, S. Wirth, P. Knochel, Org. Lett. 2006, 8, 725;
11. k) S. Sase, M. Jaric, A. Metzger, V. Malakhov, P. Knochel, J. Org. Chem. 2008, 73, 7380;
12. l) G. C. Fu, Acc. Chem. Res. 2008, 41, 1555;
13. m)C. Fischer, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 4594;
14. n) S. Son, G. C. Fu, J. Am. Chem. Soc. 2008, 130, 2756;
15. o) Y.-Q. Fang, M. Lautens, J. Org. Chem. 2008, 73, 538;
16. p) G. Dai, R. C. Larock, J. Org. Chem. 2003, 68, 920.
17. a) K. Tsutsumi, S. Ogoshi, K. Kakiuchi, S. Nishiguchi, H. Kurosawa, Inorg. Chim. Acta 1999, 296, 37;
18. b) J. Tsuji, T. Mandai, Angew. Chem. 1995, 107, 2830;
19. Angew. Chem. Int. Ed. Engl. 1995, 34, 2589, and refrences therein;
20. c) For a recent monograph on the preparation and reactivity of propargyl/allenyl zinc species, see: J. A. Marshall in The Chemistry of Organozinc Compounds (Eds.: Z. Rappoport, I. Marek), Wiley, New York, 2006, Chapter 10.
21. a) S. Ma, Eur. J. Org. Chem. 2004, 1175;
22. b) N. Yasuda, J. Organomet. Chem. 2002, 653, 279.
23. For a review of Negishi cross-coupling reactions, see: E. Negishi, Q. Hu, Z. Huang, G. Wang, N. Yin in The Chemistry of Organozinc Compounds (Eds.: Z. Rappoport, I. Marek), Wiley, New York, 2006, Chapter 11.
24. a) S. Ma, A. Zhang, Y Yu, W. Xia, J. Org. Chem. 2000, 65, 2287;
25. b) S. Ma, A. Zhang, J. Org. Chem. 2002, 67, 2287.
26. S. Ma, G. Wang, Angew. Chem. 2003, 115, 4347;
27. Angew. Chem. Int. Ed. 2003, 42, 4215.
28. For definitive studies on the structure of propargyl/allenyl lithium species, see: a) H. J. Reich, J. E. Holladay, T. G. Walker, J. L. Thompson, J. Am. Chem. Soc. 1999, 121, 9769;
29. b) H. J. Reich, J. L. Thompson, Org. Lett. 2000, 2, 783.
30. a) S. Ma, Q. He, Angew. Chem. 2004, 116, 1006;
31. Angew. Chem. Int. Ed. 2004, 43, 988;
32. b) S. Ma, Q. He, X. Zhang, J. Org. Chem. 2005, 70, 3336;
33. c) S. Ma, Q. He, X. Jin, Synlett 2005, 514.
34. For examples of the ligand effect on regioselectivity, see: a) S. Kumar Nune, M. Tanaka, Chem. Commun. 2007, 2858;
35. b) E. Zuidema, E. Daura-Oller, J. J. Carbó, C. Bo, P. W. N. M. van Leeuwen, Organometallics 2007, 26, 2234;
36. c) C. López, S. Pérez, X. Solans, M. Font-Bardía, A. Roig, E. Molins, P. W. N. M. van Leeuwen, G. P. F. van Strijdonck, Organometallics 2007, 26, 571;
37. d) T.-S. Lai, S. K. S. Lee, L.-L. Yeung, H.-Y. Liu, I. D. Williams, C. K. Chang, Chem. Commun. 2003, 620;
38. e) R. J. van Haaren, P. H. Keeven, L. A. van der Veen, K. Goubitz, G. P. F. van Strijdonck, H. Oevering, J. N. H. Reek, P. C. J. Kamer, P. W. N. M. van Leeuwen, Inorg. Chim. Acta 2002, 327, 108;
39. f) H. K. Reinius, A. O. I. Krause, Catal. Lett. 2000, 70, 149;
40. g) Y. Xia, A. S. Dudnik, V. Gevorgyan, Y. Li, J. Am. Chem. Soc. 2008, 130, 6940;
41. h) W. Cabri, I. Candiani, A. Bedeschi, R. Santi, J. Org. Chem. 1992, 57, 3558;
42. i) W. Cabri, I. Candiani, A. Bedeschi, R. Santi, J. Org. Chem. 1990, 55, 3654;
43. j) S. G. Pyne, Z. Dong, Tetrahedron Lett. 2000, 41, 5387;
44. k) J. W. Faller, J. C. Wilt, J. Parr, Org. Lett. 2004, 6, 1301.
45. P. Knochel, C. J. Rao, Tetrahedron 1993, 49, 29.
46. G. A. Molander, E. M. Sommers, S. R. Baker, J. Org. Chem. 2006, 71, 1563.
47. a) A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000,122, 4020;
48. b) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550.
49. A similar coupling product was observed for the reaction of 1-phe-nylprop-1-yne. See ref. [5a].
50. M. Zembayashi, K. Tamao, M. Kumada, Tetrahedron Lett. 1975, 16, 1719.
51. The Sonagashira coupling reaction of iodopropenoates with alkynes is stereoselective; see: R. Takeuchi, K. Tanabe, S. Tanaka, J. Org. Chem. 2000, 65, 1558.
52. Retention of configuration was observed in the propargyl/alkenyl coupling product (Z)-5 in an analogous reaction, see ref. [6].
53. A. S. Batsanov, J. P. Knowles, B. Samsam, A. Whiting, Adv. Synth. Catal. 2008, 350, 227.