Synthesis of N,N-dimethylamines via Barbier-Grignard-type electrophilic amination

Synthetic Communications

Volumn 36, Issue 19, 2006, Pages 2813-2818

  Erdik, Ender ^a   Ateş, Selma ^a  

^a ANKARA UNIVERSITY   (Turkey)

Author keywords

Barbier Grignard reaction; Electrophilic amination; N,N dimethylanilines; Tertiary amines

Indexed keywords

ALKYL GROUP; ALLYL COMPOUND; BENZYL MAGNESIUM BROMIDE; BROMINE DERIVATIVE; DIMETHYLAMINE; DIMETHYLAMINE DERIVATIVE; HEXYL MAGNESIUM BROMIDE; HYDROXYLAMINE; N,N DIMETHYL O (MESITYLENESULFONYL)HYDROXYLAMINE; N,N DIMETHYLANILINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; BARBIER GRIGNARD REACTION; GRIGNARD REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 33750065390     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910600770615     Document Type: Article

References (33)

1. Lawrence, S. A. Amines: Synthesis, Properties, and Applications; Cambridge University Press, 2004.
2. Ricci, A. (Ed.). Modern Amination Methods; Wiley, 2000.
3. (a) Kelkar, A. A.; Patil, N. M.; Chaudhari, R. V. Copper catalyzed amination of aryl halides: Single step synthesis of arylamines. Tetrahedron Lett. 2002, 43, 7143-7146;
4. (b) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Formation of aryl-nitrogen, aryl-oxygen and aryl-carbon bonds using well defined copper(I) based catalysts. Org. Lett. 2001, 3, 4135-4317;
5. (c) Goodbrand, H. B.; Hu, N.-X. Ligand accelerated catalysis of the Ullmann condensation: Application to hole conducting triarylamines. J. Org. Chem. 1999, 64, 670-674;
6. (d) Kwong, F. Y.; Buchwald, S. L. Mild and efficient copper-catalyzed amination of aryl bromides with primary alkylamines. Org. Lett. 2003, 5, 793-796.
7. (a) Wolfe, J. P.; Wagow, S.; Marcoux, J.-F.; Buchwald, S. L. Rational development of practical catalyst for aromatic carbon-nitrogen bond formation. Acc. Chem. Res. 1998, 31, 805-818;
8. (b) Hartwig, J. F. Carbon-heteroatom bondforming reductive eliminations of amines, ethers and sulfides. Acc. Chem. Res. 1998, 31, 852-860;
9. (c) Hartwig, J. F. Transition metal catalyzed synthesis of arylamines and aryl ethers from aryl halides and triflates. Angew. Chem. Int. Ed. 1998, 37, 2046-2067;
10. (d) Kuwahara, K.; Nakano, K.; Nozaki, K. Double N-arylation of primary amines: Carbazole synthesis from 2,2′-biphenyldiols. J. Org. Chem. 2005, 70, 413-419.
11. (a) Hartwig, J. F. In Handbook of Palladium Chemistry for Organic Synthesis; Negishi, E.-I., (Ed.); Wiley, 2002, Vol. 1, p. 1051;
12. (b) Mucci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131-209.
13. 3 system. Org. Lett. 2005, 7, 2209-2211.
14. Mulzer, J.; Altenbach, H. J.; Brown, M.; Krohn, K.; Reissing, H. U. In Organic Synthesis Highlights; VCH, 1911, p. 45.
15. Boche, G. In Houben-Weyl, Methods of Organic Chemistry; Helmchen, G., Hoffman, R. W., Mulzer, J., Schaumann, E., (Eds).; Theime, 1955, Vol. E21e, p. 5153.
16. Askani, R.; Taber, D. F. Comprehensive Organic Synthesis; Trost, B. M., (Ed.); Pergamon, 1996, Vol. 7, p. 1881.
17. Erdik, E.; Ay, M. Electrophilic amination of carbanions. Chem. Rev. 1989, 89, 1947-1980.
18. Genet, J. P.; Greck, C. Electrophilic amination: New synthetic applications. Synlett 1997, 741-747.
19. Dembech, P.; Seconi, G.; Ricci, A. The electrophilic amination of carbanions: An unconventional new entry to C-N bond formation. Chem. Eur. J. 2002, 6, 1281-1286.
20. Erdik, E. Electrophilic α-amination of carbonyl compounds. Tetrahedron 2004, 60, 8747-8782.
21. Greck, C.; Drouillat, B.; Thomasigny, C. Asymmetric electrophilic α-amination of carbonyl compounds. Eur. J. Chem. 2004, 10, 1377.
22. Greck, C.; Bischoff, L.; Ferreira, F.; Genet, J. P. Preparation and reactivity of ally N-[(arylsulfonyl)oxy]carbamates: New reagents for electrophilic transfer of on NHAlloc group. J. Org. Chem. 1995, 60, 7010-7012.
23. Boche, G.; Mayer, N.; Bernheim, M.; Wagner, K. Electrophilic amination of carbanions with N,N-dialkyl O-(arylsulphonyl)hydroxylamines. Angew. Chem. Int. Ed. 1978, 17, 687.
24. Boche, G.; Bernheim, M.; Niessner, M. 1-Alkinylamines by electrophilic amination. Angew. Chem. Int. Ed. 1983, 22, 53-54.
25. Bernheim, M.; Boche, G. Electrophilic amination of cyclopentadienyllithium compounds. Angew. Chem. Int. Ed. 1980, 19, 1010-1011.
26. Abraham, T.; Curran, D. Formation and amination of dibenz [b, f-1] azapentalene dianion. Tetrahedron 1982, 38, 1019.
27. Berman, A. M.; Johnson, J. S. Copper catalyzed amination of diorganozinc reagents. J. Am. Chem. Soc. 2004, 126, 5680-5681.
28. Berman, A. M.; Johnson, J. S. Copper catalyzed electrophilic amination of functionalized diarylzinc reagents. J. Org. Chem. 2005, 70, 364-366.
29. Berman, A. M.; Johnson, J. S. Nickel catalyzed electrophilic amination of organozinc halides. Synlett 2005, 1799-1801.
30. Erdik, E.; Daşkapan, T. Can ve aminate Grignard reagents under Barbier conditions? Tetrahedron Lett. 2002, 43, 6237-6239.
31. (a) Erdik, E.; Ay, M. Effect of copper (I) iodide and magnesium chloride on amination of aryl Grignard reagents with ketoximes. Synth. React. Inorg. Metal-Org. Chem. 1989, 19, 663-668;
32. (b) Erdik, E.; Daşkapan, T. Electrophilic amination of diarylzincs and triarylzincates with acetone O-(2,4,6-trimethylphenyl sulfonyl)oxime and O-methylhydroxylamine. Synth. Commun. 1999, 29, 3989-3998;
33. (c) Erdik, E.; Daşkapan, T. Electrophilic amination of organozinc reagents with acetone O-(2,4,6-trimethylphenylsulfonyl)oxime and O-methylhydroxylamine. J. Chem. Soc. Perkin Trans. 1999, 3139-3142.