Iron/amino acid catalyzed direct N-alkylation of amines with alcohols

Angewandte Chemie - International Edition

Volumn 50, Issue 13, 2011, Pages 3006-3009

  Zhao, Yingsheng ^a   Foo, Siong Wan ^a   Saito, Susumu ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Alcohols; Amino acids; Homogeneous catalysis; Iron; N alkylation

Indexed keywords

ACID CATALYSIS; CARBON ATOMS; CHEMICAL EQUATIONS; HOMOGENEOUS CATALYSIS; HYDROXY GROUPS; N-ALKYLATION; NEAR-NEUTRAL PH;

AMINATION; AMINO ACIDS; CATALYSIS; REACTION KINETICS;

ALKYLATION;

ALCOHOL DERIVATIVE; AMINE; AMINO ACID; IRON;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; ALKYLATION; AMINES; AMINO ACIDS; CATALYSIS; IRON; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 79952640140     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201006660     Document Type: Article

References (49)

1. a) A. Seayad, M. Ahmed, H. Klein, R. Jackstell, T. Gross, M. Beller, Science 2002, 297, 1676-1678;
2. b) S. A. Lawerencem, Amines: Synthesis Properties and Applications, Cambridge University, Cambridge, 2004;
3. c) B. R. Brown, The Organic Chemistry of Aliphatic Nitrogen Compounds, Cambridge University, Cambridge, 2004.
4. Reviews: a) M. H. S. A. Hamid, P. A. Slatford, J. M. J. Williams, Adv. Synth. Catal. 2007, 349, 1555-1575;
5. b) T. D. Nixon, M. K. Whittlesey, J. M. J. Williams, Dalton Trans. 2009, 753-762;
6. c) G. Guillena, D. J. Ramón, M. Yus, Chem. Rev. 2010, 110, 1611-1641;
7. d) G. E. Dobereiner, R. H. Crabtree, Chem. Rev. 2010, 110, 681-703.
8. Selected examples: a) S. Murahashi, K. Kondo, T. Hakata, Tetrahedron Lett. 1982, 23, 229-232;
9. b) Y. Watanabe, Y. Tsuji, H. Ige, Y. Ohsugi, T. Ohta, J. Org. Chem. 1984, 49, 3359-3363;
10. c) A. Tillack, D. Hollmann, K. Mevius, D. Michalik, S. Bähn, M. Beller, Eur. J. Org. Chem. 2008, 4745-4750;
11. d) M. H. S. A. Hamid, J. M. J. Williams, Chem. Commun. 2007, 725-727;
12. e) S. Naskar, M. Bhattacharjee, Tetrahedron Lett. 2007, 48, 3367-3370;
13. f) S. Bähn, D. Hollmann, A. Tillack, M. Beller, Adv. Synth. Catal. 2008, 350, 2099-2103;
14. g) C. Gunanathan, D. Milstein, Angew. Chem. 2008, 120, 8789-8792;
15. Angew. Chem. Int. Ed. 2008, 47, 8661-8664;
16. 4:
17. i) F. Shi, M. K. Tse, S. Zhou, M.-M. Pohl, J. Radnik, S. Hübner, K. Jähnisch, A. Brückner, M. Beller, J. Am. Chem. Soc. 2009, 131, 1775-1779;
18. j) B. Gnanaprakasam, J. Zhang, D. Milstein, Angew. Chem. 2010, 122, 1510-1513;
19. Angew. Chem. Int. Ed. 2010, 49, 1468-1471;
20. k) S. Imm, S. Bähn, L. Neubert, H. Neumann, M. Beller, Angew. Chem. 2010, 122, 8303-8306;
21. Angew. Chem. Int. Ed. 2010, 49, 8126-8129.
22. a) K.-i. Fujita, K. Yamamoto, R. Yamaguchi, Org. Lett. 2002, 4, 2691-2694;
23. b) K.-i. Fujita, Y. Enoki, R. Yamaguchi, Tetrahedron 2008, 64, 1943-1954;
24. c) B. Blank, M. Madalska, R. Kempe, Adv. Synth. Catal. 2008, 350, 749-758;
25. d) D. Balcells, A. Nova, E. Clot, D. Gnanamgrai, R. H. Crabtree, O. Eisenstein, Organometallics 2008, 27, 2529-2535;
26. e) B. Blank, S. Michlik, R. Kempe, Adv. Synth. Catal. 2009, 351, 2903-2911;
27. f) H. Aramoto, Y. Obora, Y. Ishii, J. Org. Chem. 2009, 74, 628-633;
28. g) B. Blank, R. Kempe, Chem. Eur. J. 2009, 15, 3790-3799.
29. Copper/aluminum hydrotalcite: a) P. R. Likhar, ; R. Arundhathi, M. L. Kantam, P. S. Prathima, Eur. J. Org. Chem. 2009, 5383-5389;
30. R. Arundhathi, M. L. Kantam, P. S. Prathima, Eur. J. Org. Chem. 2009, 5383-5389;
31. b) F. Shi, M. K. Tse, X. Cui, D. Gördes, D. Michalik, T. Y. Deng, M. Beller, Angew. Chem. 2009, 121, 6026-6029;
32. Angew. Chem. Int. Ed. 2009, 48, 5912-5915;
33. c) X. Cui, F. Shi, M. K. Tse, D. Gördes, K. Thurow, M. Beller, Y. Deng, Adv. Synth. Catal. 2009, 351, 2949-2958.
34. B. Sreedhar, P. S. Reddy, M. A. Reddy, B. Neelima, R. Arundhathi, Tetrahedron Lett. 2007, 48, 8174-8177.
35. A. Correa, O. G. Manecheno, C. Bolm, Chem. Soc. Rev. 2008, 37, 1108-1117.
36. a) F. Ozawa, H. Okamoto, S. Kawagishi, S. Yamamoto, T. Minami, M. Yoshifuji, J. Am. Chem. Soc. 2002, 124, 10968-10969;
37. b) Y. Yamashita, A. Gopalarathnam, J. F. Hartwig, J. Am. Chem. Soc. 2007, 129, 7508-7509;
38. c) M. Utsunomiya, Y. Miyamoto, J. Ipposhi, T. Ohshima, K. Mashima, Org. Lett. 2007, 9, 3371-3374.
39. a) V. Terrasson, S. Marque, M. Georgy, J.-M. Campagne, D. Prim, Adv. Synth. Catal. 2006, 348, 2063-2067;
40. b) H. Qin, N. Yamagiwa, S. Matsunaga, M. Shibasaki, Angew. Chem. 2007, 119, 413-417;
41. Angew. Chem. Int. Ed. 2007, 46, 409-413;
42. c) C. R. Reddy, P. P. Madhavi, A. S. Reddy, Tetrahedron Lett. 2007, 48, 7169-7172;
43. d) U. Jana, S. Maiti, S. Biswas, Tetrahedron Lett. 2008, 49, 858-862.
44. a) M. Noji, T. Ohno, K. Fuji, N. Futaba, H. Tajima, K. Ishii, J. Org. Chem. 2003, 68, 9340-9347;
45. b) I. Iovel, K. Mertins, J. Kischel, A. Zapf, M. Beller, Angew. Chem. 2005, 117, 3981-3985;
46. Angew. Chem. Int. Ed. 2005, 44, 3913-3917;
47. c) J. S. Yadav, D. C. Bhunia, K. V. Krishna, P. Srihari, Tetrahedron Lett. 2007, 48, 8306-8310.
48. P. Rubenbauer, T. Bach, Adv. Synth. Catal. 2008, 350, 1125-1130.
49. 3/4a·amine as a weak acid and amine as a weak base, both should be working cooperatively.