Iron-Catalyzed Reductive Aryl-Alkenyl Cross-Coupling Reactions

ChemCatChem

Volumn 3, Issue 1, 2011, Pages 135-138

  Czaplik, Waldemar M ^a   Mayer, Matthias ^a   JacobivonWangelin, Axel ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

Cross coupling; Domino reactions; Grignard reactions; Iron; Styrenes

Indexed keywords

EID: 80051824396     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201000276     Document Type: Article

References (57)

1. Metal-Catalyzed Cross-Coupling Reactions (Eds: A. deMeijere, F. Diederich), Wiley-VCH, Weinheim, 2004;
2. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4516-4563; Angew. Chem. Int. Ed. 2005, 44, 4442-4489.
3. For timely reviews, see:
4. W. M. Czaplik, M. Mayer, J. Cvengroš, A. Jacobi von Wangelin, ChemSusChem 2009, 2, 396-407;
5. B. D. Sherry, A. Fürstner, Acc. Chem. Res. 2008, 41, 1500-1511;
6. A. Correa, O. G. Mancheno, C. Bolm, Chem. Soc. Rev. 2008, 37, 1108-1117;
7. E. B. Bauer, Curr. Org. Chem. 2008, 12, 1341-1369.
8. S. E. Denmark, C. R. Butler, Chem. Commun. 2009, 20-33;
9. The Mizoroki-Heck Reaction (Ed: M. Oestreich), Wiley, Chichester, 2009.
10. For example, stilbenoid phytoalexines (resveratrol), cinnamates, and flavonoid plant pigments. For the physiology and biosynthesis of phenylpropanoid metabolites, see: K. Hahlbrock, D. Scheel, Annu. Rev. Plant Physiol. Plant Mol. Biol. 1989, 40, 347-369.
11. An overview of industrial arylalkene intermediates (e.g. the sun-screen agent EHMC, the herbicide Prosulfuron, the antihistamine Montelukast-Na, and electronic cyclotene resins): A. Zapf, M. Beller, Top. Catal. 2002, 19, 101-109;
12. Synthesis of heterocycles: R. C. Larock, P. Pace, H. Yang, C. E. Russell, S. Cacchi, G. Fabrizi, Tetrahedron 1998, 54, 9961-9980;
13. Polymers: A. Hirao, S. Loykulnant, T. Ishizone, Prog. Polym. Sci. 2002, 27, 1399-1471.
14. Iron-catalyzed alkenylations have been predominantly performed with alkylmagnesium halides (see refs.[2a] and [10]). For selected examples of aryl-alkenyl coupling reactions, see:
15. S. M. Neumann, J. K. Kochi, J. Org. Chem. 1975, 40, 599-606;
16. H. Felkin, B. Meunier, J. Organomet. Chem. 1978, 146, 169-178;
17. G. A. Molander, B. J. Rahn, D. C. Shubert, Tetrahedron Lett. 1983, 24, 5449-5452;
18. E. Alvarez, T. Cuvigny, H. du Ponhoat, M. Julia, Tetrahedron 1988, 44, 119-126;
19. A. Fürstner, H. Brunner, Tetrahedron Lett. 1996, 37, 7009-7012;
20. W. Dohle, F. Kopp, G. Cahiez, P. Knochel, Synlett 2001, 1901-1903;
21. B. Scheiper, M. Bonnekessel, H. Krause, A. Fürstner, J. Org. Chem. 2004, 69, 3943-3949;
22. K. Itami, S. Higashi, M. Mineno, J.-i. Yoshida, Org. Lett. 2005, 7, 1219-1222;
23. U. S. Larsen, L. Martiny, M. Begtrup, Tetrahedron Lett. 2005, 46, 4261-4263;
24. G. Dunet, P. Knochel, Synlett 2006, 407-410.
25. -1; taken from: CRC Handbook of Chemistry and Physics (Eds: R.C. Weast, M.J. Astle), CRC Press, Boca Raton, 1981;
26. 2+:-2.38V (SCE); taken from: Handbook of Grignard Reagents (Eds: G.S. Silverman, P.E. Rakita), Dekker, New York, 1996, p.13.
27. For iron-catalyzed Grignard formation, see: B. Bogdanovic, M. Schwickardi, Angew. Chem. 2000, 112, 4788-4790; Angew. Chem. Int. Ed. 2000, 39, 4610-4612;
28. W. M. Czaplik, M. Mayer, A. JacobivonWangelin, Angew. Chem. 2009, 121, 616-620; Angew. Chem. Int. Ed. 2009, 48, 607-610;
29. W. M. Czaplik, M. Mayer, S. Grupe, A. JacobivonWangelin, Pure Appl. Chem. 2010, 82, 1545-1553.
30. For details, see the Supporting Information.
31. Cross-coupling reactions of alkenyl bromides with primary alkyl-MgX proceed with retention of double bond configuration. See for example:
32. G. Cahiez, H. Avedissian, Synthesis 1998, 1199-1205;
33. G. Cahiez, S. Marquais, Tetrahedron Lett. 1996, 37, 1773-1776;
34. Reactions with arylmagnesium halides and sterically demanding Alkyl-MgX experience at least partial double bond isomerization, see for example [6c].
35. Selected examples:
36. M. S. Kharasch, E. K. Fields, J. Am. Chem. Soc. 1941, 63, 2316-2320;
37. T. Nagano, T. Hayashi, Org. Lett. 2005, 7, 491-493;
38. G. Cahiez, C. Chaboche, F. Mahuteau-Betzer, M. Ahr, Org. Lett. 2005, 7, 1943-1946;
39. X. Xu, D. Cheng, W. Pei, J. Org. Chem. 2006, 71, 6637-6639;
40. M. Mayer, W. M. Czaplik, A. JacobivonWangelin, Synlett 2009, 2919-2923.
41. F. M. Piller, A. Metzger, M. A. Schade, B. A. Haag, A. Gavryushin, P. Knochel, Chem. Eur. J. 2009, 15, 7192-7202;
42. N. Boudet, S. Sase, P. Sinha, C.-Y. Liu, A. Krasovskiy, P. Knochel, J. Am. Chem. Soc. 2007, 129, 12358-12359.
43. U. Tilstam, H. Weinmann, Org. Process Res. Dev. 2002, 6, 906-910.
44. S. L. Buchwald, C. Bolm, Angew. Chem. 2009, 121, 5694-5695; Angew. Chem. Int. Ed. 2009, 48, 5586-5587;
45. R. B. Bedford, M. Nakamura, N. J. Gower, M. F. Haddow, M. A. Hall, M. Huwea, T. Hashimoto, R. A. Okopie, Tetrahedron Lett. 2009, 50, 6110-6111.
46. Safety aspects of Grignard species:
47. J. T. Reeves, M. Sarvestani, J. J. Song, Z. Tan, L. J. Nummy, H. Lee, N. K. Yee, C. H. Senanayake, Org. Process Res. Dev. 2006, 10, 1258-1262;
48. H. Kryk, G. Hessel, W. Schmitt, Org. Process Res. Dev. 2007, 11, 1135-1140.
49. Selected examples:
50. D. A. Everson, R. Shrestha, D. J. Weix, J. Am. Chem. Soc. 2010, 132, 920-921;
51. A. Krasovskiy, C. Duplais, B. H. Lipshutz, J. Am. Chem. Soc. 2009, 131, 15592-15593;
52. W. M. Czaplik, M. Mayer, A. Jacobi von Wangelin, Synlett 2009, 2931-2934;
53. M. Amatore, C. Gosmini, Chem. Commun. 2008, 5019-5021.
54. For discussion of the nature of iron catalysts and possible mechanistic scenarios, see:
55. G. Cahiez, V. Habiak, C. Duplais, A. Moyeux, Angew. Chem. 2007, 119, 4442-4444; Angew. Chem. Int. Ed. 2007, 46, 4364-4366;
56. A. Fürstner, R. Martin, H. Krause, G. Seidel, R. Goddard, C. W. Lehmann, J. Am. Chem. Soc. 2008, 130, 8773-8787;
57. D. Noda, Y. Sunada, T. Hatakeyama, M. Nakamura, H. Nagashima, J. Am. Chem. Soc. 2009, 131, 6078-6079.