Selective copper-promoted cross-coupling of aromatic amines with alkyl boronic acids

Synlett

Volumn , Issue 14, 2010, Pages 2101-2105

  Larrosa, Marta ^a   Guerrero, César ^a   Rodríguez, Ramón ^a   Cruces, Jacobo ^a  

^a R and D Department   (Spain)

Author keywords

alkylation; amines; boron; copper; cross coupling

Indexed keywords

AROMATIC AMINE; BORONIC ACID DERIVATIVE; N (2 PHENYLETHYL)PYRIDIN 3 AMINE; N (2 PHENYLETHYL)QUINOLIN 3 AMINE; N (2 PHENYLETHYL)QUINOLIN 8 AMINE; N (4 CHLOROPHENYL) N PROPYLAMINE; N (4 METHOXYPHENYL) N PROPYLAMINE; N (4 METHYLPHENYL) N (2 PHENYLETHYL)AMINE; N (4 TERT BUTYLPHENYL) N PROPYLAMINE; UNCLASSIFIED DRUG;

ACIDITY; ALKYLATION; AMINATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CROSS COUPLING REACTION; REACTION TIME; SYNTHESIS;

EID: 77956031553     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1258523     Document Type: Article

References (44)

1. (a) Negwer M, Organic-Chemical Drugs and their Synonyms (An International Survey) 7th ed. Akademie Verlag GmbH Berlin 1994
2. (b) Montgomery J H., Agrochemicals Desk Reference: Environmental Data Lewis Publishers Chelsea MI 1993
3. (c) The Chemistry of Anilines Vol. 1 Rappoport Z Wiley-Interscience New York 2007
4. (a) Watanabe Y, Tsuji Y, Ohsugi Y, Tetrahedron Lett. 1981 22 2667
5. (b) Watanabe Y, Tsuji Y, Ige H, Ohsugi Y, Ohta T, J. Org. Chem. 1984 49 3359
6. (c) Watanabe Y, Morisaki Y, Kondo T, Mitsudo T.-A, J. Org. Chem. 1996 61 4214
7. (d) Jun C, Hwang D, Na S, Chem. Commun. 1998 1405
8. (e) Abbenhuis R A. T. M., Boersma J, vanKoten G, J. Org. Chem. 1998 63 4282; and references cited therein
9. (f) Naota T, Takaya H, Murahashi S.-I, Chem. Rev. 1998 98 2599
10. (g) Grigg R, Mitchell T R. B., Sutthivaiyakit S, Tongpenyai N, [nl] J. Chem. Soc., Chem. Commun. 1981 611
11. (h) Cami-Kobeci G, Williams J M. J., Chem. Commun. 2004 1072
12. (i) Fujita K.-I, Yamaguchi R, Synlett 2005 560
13. (j) Yamaguchi R, Kawagoe S, Asai C, Fujita K.-I, Org. Lett. 2008 10 181
14. (k) Hollmann D, Bähn S, Tillack A, Beller M, Angew. Chem. Int. Ed. 2007 46 8291
15. (l) Tillack A, Hollmann D, Michalik D, Beller M, Tetrahedron Lett. 2006 47 8881
16. (m) Fujita K, Enoki Y, Yamaguchi R, Tetrahedron 2008 64 1943
17. (n) Hamid M H., Allen L, Lamb G W., Maxwell A C., Maytum [nl]H C., Watson A J. A., Williams J M. J., J. Am. Chem. Soc. 2009 131 1766
18. (a) Müller T E., Beller M, Chem. Rev. 1998 98 675
19. (b) Beller M, Trauthwein H, Eichberger M, Breindl C, Herwig J, Müller T E., Thiel O R., Chem. Eur. J. 1999 5 1306
20. (c) Nobis M, Driessen-Hölscher B, Angew. Chem. Int. Ed. 2001 40 3983
21. (d) Utsunomiya M, Kuwano R, Kawatsura M, Hartwig J F., J. Am. Chem. Soc. 2003 125 5608
22. (e) Ryu J.-S, Li G Y., Marks T J., J. Am. Chem. Soc. 2003 125 12584
23. (f) Johns A M., Utsunomiya M, Incarvito C D., Hartwig J F., J. Am. Chem. Soc. 2006 128 1828
24. (a) Chan D M. T., Monaco K L., Wang R P., Winters [nl]M P., Tetrahedron Lett. 1998 39 2933
25. (b) Evans D A., Katz J L., West T R., Tetrahedron Lett. 1998 39 2937
26. (c) Lam P Y. S., Clark C G., Saubern S, Adams J, Winters M P., Chan D M. T., Combs A, Tetrahedron Lett. 1998 39 2941
27. (d) Lam P Y. S., Clark C G., Saubern S, Adams J, Averill K M., Chan D M. T., Combs A, Synlett 2000 674
28. (a) For reviews on copper-mediated carbon-heteroatom bond formations, see:, Ley S V., Thomas A W., Angew. Chem. Int. Ed. 2003 42 5400
29. (b) Beletskaya I P., Cheprakov A V., Coord. Chem. Rev. 2004 248 2337
30. (a) Collman J P., Zhong M, Org. Lett. 2000 2 1233
31. (b) Antilla J C., Buchwald S L., Org. Lett. 2001 3 2077
32. (c) Lam P Y. S., Vincent G, Clark C G., Deudon S, Jadhav P K., Tetrahedron Lett. 2001 42 3415
33. (a) Moessner C, Bolm C, Org. Lett. 2005 7 2667
34. (b) Lan J.-B, Zhang G.-L, You J.-S, Chen L, Yan M, Xie R.-G, Synlett 2004 1095
35. (c) Sreedhar B, Venkanna G T., Kumar K B. S., Balasubrahmanyam V, Synthesis 2008 795
36. (a) Tsuritani T, Strotman N A., Yamamoto Y, Kawasaki M, Yasuda N, Mase T, Org. Lett. 2008 10 1653
37. (b) Bérnard S, Neuville L, Zhu J, J. Org. Chem. 2008 73 6441
38. (c) For the use of cyclohexylboronic acid, see: Boronic Acids 1st ed. Hall D G. Wiley-VCH Weinheim 2005 Chap. 5
39. González I, Mosquera J, Guerrero C, Rodríguez R, Curces J, Org. Lett. 2009 11 1677
40. Patrick G L., In An Introduction to Medicinal Chemistry 2nd ed. Oxford University Press Oxford 2001 69
41. (a) Heutling A, Pohlki F, Bytschkov I, Doye S, Angew. Chem. Int. Ed. 2005 44 2951
42. (b) Hamid M H. S. A., Williams J M. J., Chem. Commun. 2007 725
43. (c) Munro-Leighton C, Delp S A., Alsop N M., Blue E D., Gunnoe T B., Chem. Commun. 2008 111
44. (d) Iranpoor N, Firouzabadi H, Nowrouzi N, Khalili D, Tetrahedron 2009 65 3893