Chemoselective C-H bond activation: Ligand and solvent free iron-catalyzed oxidative C-C cross-coupling of tertiary amines with terminal alkynes. Reaction scope and mechanism

Organic Letters

Volumn 11, Issue 8, 2009, Pages 1701-1704

  Volla, Chandra M Rao ^a   Vogel, Pierre ^a  

^a EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AMINE; DRUG DERIVATIVE; FERROUS CHLORIDE; FERROUS ION; PARGYLINE; PROPARGYLAMINE; PROPYLAMINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALKYNES; AMINES; CATALYSIS; FERROUS COMPOUNDS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PARGYLINE; PROPYLAMINES;

EID: 65249127058     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9002509     Document Type: Article

References (72)

1. (a) Dvker. G. Handbook of C-H Transformations; Wiley-VCH: Weinheim, 2005.
2. (b) Li, C. J.; Li, Z. P. Pure Appl. Chem. 2006, 78, 935- 945.
3. (c) Ackermann, L.; Althammer, A.; Born, R. Angew. Chem., Int. Ed. 2006, 45, 2619-2622.
4. (d) Company, A.; Gómez, L.; Güell, M.; Ribas. X.; Luis. J. M.; Que, L.; Jr.; Costas, M. J. Am. Chem. Soc. 2007, 129, 15766- 15767.
5. (e) Campos, K. R. Chem. Soc. Rev. 2007, 36, 1069-1084.
6. (f) Lewis. J. C; Bergman. R. G.; Ellman. J. A. Acc. Chem. Res. 2008, 41, 1013- 1025.
7. (g) Li, B. J.; Yang, S. D.; Shi, Z. J. Synlett 2008, 949-957.
8. (h) Park, Y. J.; Park. J. W.; Jun, C. H. Acc. Chem. Res. 2008, 41, 222-234.
9. (i) Herrerias, C. I.; Yao, X. Q.; Li, Z. P.; Li, C. J. Chem. Rev. 2007, 107, 2546-2562.
10. de Paolini, 1.; Ribet, G. Gazz. Chim. Ital. 1932, 62, 1041-1048.
11. Horner, L.; Schwenk. E. Ann. Chem. Justus Liebig 1950, 566, 69-84.
12. (a) Horner, L.; Junkermann, H. Ann. Chem. Justus Liehig 1955, 59l, 53-68.
13. (b) Horner, L.; Kirmse, W. Ann. Chem. Justus Liehig 1955, 597, 48-65.
14. Lalevee, J.; Allonas, X.; Fouassier, J. P.; lngold. K. U. J. Org. Chem. 2008, 73, 6489-6496.
15. (a) Galliani, G.; Rindone, B.; Marchesini. A. J. Chem. Soc, Perkin Trans. I 1978, 456-460.
16. (b) Galliani, G.; Rindone, B. J. Chem. Soc, Perkin Trans. 2 1980, 1-3.
17. (a) Guengerich, F. P.; MacDonald, T. L. Acc. Chem. Res. 1984, 17, 9-16.
18. (b) Baciocchi, E.; Gerini, M. F.; Lapi, A. Chem. Commun. 2002, 946-947.
19. (c) Baciocchi, E.; Gerini. M. F.; Lanzalunga, O.; Lapi, A.; Lo Piparo, M. G.; Mancinelli, S. Eur. j. Org. Chem. 2001, 230, 5-2310.
20. (a) Cytochrome P-450. 2nd ed.: Plenum: New York, 1995. (b) Cuppoletti, A.; Galli, C; Gentili, P.; Petride, H. J. Phys. Org. Chem. 2002, 15, 672-675.
21. (c) Urlacher, V. B.; Bell, S. G.; Wong, L. L. Mod. Biooxid. 2007, 99-122.
22. (d) Chiavarino. B.; Cipollini. R.; Crestoni. M. E.; Fornarini. S.; Lanucara, F.; Lapi, A. J. Am. Chem. Soc. 2008, 130, 3208-3217.
23. Murahashi. S.: Naota. T.; Yonemura, K. J. Am. Chem. Soc. 1988, 110, 8256-8258.
24. Murahashi, S. L; Nakae, T.; Terai, H.; Komiya, N. J. Am. Chem. Soc. 2008, 130, 11005-11012, and references therein.
25. For other metal-catalyzed α-C-H activation of tertiary amines, see:
26. (a) Wilson, R. B., Jr.; Laine, R. M. J.Am. Chem. Soc. 1985, 107, 361-369.
27. (b) Chatani, N.; Asaumi, T.; Yorimitsu, S.; Ikeda, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2001, 123, 10935-10941.
28. (c) DeBoef, B.; Pastine, S. J.; Sames, D. J. Am. Chem. Soc 2004, 126, 6556-6557.
29. (d) Pastine. S. J.; Gribkov. D. V.; Sames. D. J. Am. Chem. Soc. 2006, 128, 14220- 14221.
30. (e) Catino, A. J.; Nichols, J. M.; Nettles, B. J.; Dovle. M. P. J. Am. Chem. Soc 2006, 128, 5648-5649.
31. (a) Murata, S.; Miura. M.; Nomura, M. J. Org. Chem. 1989, 54, 4700-4702.
32. (b) Murata. S.; Miura, M.; Nomura, M. J. Chem. Soc, Chem. Commun. 1989, 116-118.
33. Murata. S.; Teramoto. K.; Miura. M.; Nomura, M. J. Chem. Res., Synop. 1993, 434.
34. See e. g.: (a) Likhar, P. R.; Subhas, M. S.; Roy, S.; Kantam, M. L.; Sndhar. B.; Seth. R. K.; Biswas. S. Qrg. Biomol. Chem. 2009, 7, 85-93.
35. (b) Zhou. Y.; Beeler, A. B.; Cho. S.; Wang. Y.; Franzblau, S. G.; Snvder, J. K. J. Comb. Chem. 2008, 10, 534-540.
36. (c) Boulton, A. A.; Davis, B'. A.; Durden. D. A.; Dvck, L. E.; Juorio. A. V.; Li, X. M.; Paterson, I. A.; Yu. P. H. Drug Dev. Res. 1997, 42, 150-156.
37. (d) Miura, M.; Enna. M.; Okuro, K.; Nomura, M. J. Org. Chem. 1995, 60, 4999-5004.
38. Li, Z. P.; Li, C. J. J. Am. Chem. Soc. 2004, 126, 11810-11811.
39. 2-promoted oxidative α-(nitroalkylation) of tertiary amines:
40. (b) Baslé, O.; Li, C. J. Green Chem. 2007, 9, 1047-1050.
41. Li, Z. P.: Li, C. J. J. Am. Chem. Soc. 2005, 127, 6968-6969.
42. Li. Z. P.; Bohle, D. S.; Li. C. J. Proc. Nat. Acad. Sci. U.S.A. 2006, 103, 8928-8933.
43. Niu. M.; Yin, Z.; Fu, Ft.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2008, 73, 3961-3963.
44. (a) Fürstner. A.: Martin, R.; Krause. H.; Seidel, G.: Goddard. R.; Lehmann, C. W. J. Am. Chem. Soc. 2008, 130, 8773-8787, and references therein.
45. (b) Sherry. B. D.; Fürstner, A. Acc. Chem. Res. 2008, 41, 1500- 1511.
46. (c) Plietker, B. Iron Catalysis in Organic Chemistry; Wiley-VCH: Weinheim, 2008.
47. (d) Bauer, E. H. Curr. Org. Chem. 2008, 72, 1341-1369.
48. (e) Norinder. J.; Matsumoto. A.; Yoshikai, N.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 5858-5859.
49. (f) Enthaler. S.: Junge, K.; Beller. M. Angew. Chem., Int. Ed. 2008, 47, 3317-3321.
50. (g) Carril. M.; Correa, A.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 4862-4865.
51. (h) Volla, C. M. R.; Vogel, P. Angew. Chem., Int. Ed. 2008, 47, 1305-1307.
52. (i) Loska. R.: Volla. C. M. R. Adv. Synth. Catal 2008, 150, 2859-2864.
53. (j) Reymond, S.; Ferrié, L.; Guerinot, A.; Capdevielle, P.; Cossy, J. Pure Appl. Chem. 2008, 80, 1683-1691.
54. (k) Volla, C. M. R.; Vogel. P. Tetrahedron Lett. 2008, 49, 5961-5964.
55. See e. g.: (a) Lipshutz, B. H.; Ghorai, S. Aldrichimica Acta 2008, 41, 59-72.
56. (b) Marion, N.; Nolan. S. P. Acc. Chem. Res. 2008, 41, 1440- 1449.
57. (c) Surry. D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338-6361.
58. (d) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450-1460.
59. (e) Buchwald, S. L.; Martin, R. Acc. Chem. Res. 2008, 41, 1461-1473.
60. (f) Denmark, S. E.; Regens. C. S. Acc. Chem. Res. 2008, 41, 1486-1499.
61. Tanko, J. M.; Friedline, R.; Suleman, N. K.; Castagnoli, N., Jr. J. Am. Chem. Soc. 2001, 123, 5808-5809.
62. (a) Kern, W.; Schulz, R. Makromol. Chem. 1954, 13, 210-222.
63. (b) Li. Z. P.; Cao. L.; Li, C. J. Angew. Chem., Int. Ed. 2007, 46, 6505-6507.
64. (c) Zhang, Y.; Li, C. J. Eur. J. Org. Chem. 2007, 4654-4657.
65. 1H NMR spectrum, which is analogous to that N-ethyloxvmethvl-N-methylaniline Raap. J.; Nieuwenhuis, S.; Creemers. A.; Hexpoor, S.; Kragle. U.; Lugtenburg, J. Eur. J. Org. Chem. 1999, 2609-2621.
66. Deng, G.; Li, C. J. Tetrahedron Lett. 2008, 49, 5601-5604.
67. Sawver, D. T.; Sobkowiak. A.; Matsushita, T. Acc. Chem. Res. 1996, 29. 409-416.
68. 3 catalyzes conversion of terminal alkynes, aldehydes, and secondary amines into aminoalkynes, reactions that probably imply iminium ion intermediates reacting with acetylide intermediates: Li, P.; Zhang, Y.; Wang, L. Chem. Eur. J. 2009, 15, 2045-2049.
69. For aminoalkynes as potential drugs, see: (a) Pisano, C; Battistuzzi, G.; Di Marzo, M.; Giannini, G.; Marzi, M.; Vesci, L.; Zunino, F.; Pezzi, R. PCTInt. Appl. 2006: Chem. Abstr. 2006, 146, 62468.
70. (b) Fournet, G.; Quash, G. A.; Gore. J. PCTInt. Appl. 2001; Chem. Abstr. 2001, 136, 5727.
71. (c) Moon, M. W.; Heier. R. F. PCTInt. Appl. 1990; Chem. Abstr. 1990, 113, 115301.
72. (d) Adams, T. C; Dupont, A. C.; Carter, J. P.; Kachur, J. F.; Guzewska, M. E.; Rzeszotarski. W. J.; Farmer. S. G.; Noronha-Blob. L.; Kaiser, C. J. Med. Chem. 1991, 34, 1585-1593.