SCOPUS 정보 검색 플랫폼

Chemical Communications

Volumn , Issue 27, 2008, Pages 3199-3201

N-Dealkylation of aliphatic amines and selective synthesis of monoalkylated aryl amines

(4) Hollmann, Dirk a Bähn, Sebastian a Tillack, Annegret a Beller, Matthias a

a UNIVERSITY OF ROSTOCK (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ANILINE; DIBENZYLAMINE; DICYCLOHEXYLAMINE DERIVATIVE; DIISOPROPYLAMINE; DIPROPYLAMINE; TRIBENZYLAMINE; TRIETHYLAMINE;

ALKYLATION; AMINATION; ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEALKYLATION; SYNTHESIS;

EID: 46249094626 PISSN: 13597345 EISSN: None Source Type: Journal
DOI: 10.1039/b803114b Document Type: Article

Times cited : (90)

References (44)

1
- 0036039362
- Review of P450 enzymes:
- P. Hlavica Drug Metab. Rev. 2002 34 451
- (2002) Drug Metab. Rev. , vol.34 , pp. 451
- Hlavica, P.¹

2
- 27544467591
- D. Meyer T. Leifels L. Sbaragli W.-D. Woggon Biochem. Biophys. Res. Commun. 2005 338 372
- (2005) Biochem. Biophys. Res. Commun. , vol.338 , pp. 372
- Meyer, D.¹ Leifels, T.² Sbaragli, L.³ Woggon, W.-D.⁴

3
- 0002819784
- W.-D. Woggon Top. Curr. Chem. 1997 184 39
- (1997) Top. Curr. Chem. , vol.184 , pp. 39
- Woggon, W.-D.¹

4
- 2742599124
- P. Ortiz de Montellano, Plenum Press, New York, London, 2nd edn
- Cytochrome P450 Structure, Mechanism and Biochemistry, ed., P. Ortiz de Montellano,, Plenum Press, New York, London, 2nd edn, 1995
- (1995) Cytochrome P450 Structure, Mechanism and Biochemistry, Ed.

5
- 78651165715
- In organic synthesis only a few dealkylation reactions are known: for the von Braun reaction, Polonovski demethylation reaction, and others, see:
- T. Omura R. J. Sato J. Biol. Chem. 1964 239 2370
- (1964) J. Biol. Chem. , vol.239 , pp. 2370
- Omura, T.¹ Sato, R.J.²

6
- 0345529001
- and references therein
- K. McCamley J. A. Ripper R. D. Singer R. J. Scammells J. Org. Chem. 2003 68 9847
- (2003) J. Org. Chem. , vol.68 , pp. 9847
- McCamley, K.¹ Ripper, J.A.² Singer, R.D.³ Scammells, R.J.⁴

7
- 34848894339
- Z. Rappoport, Wiley-Interscience, New York, For recent examples of palladium-catalyzed aminations, see:
- The Chemistry of Anilines, ed., Z. Rappoport,, Wiley-Interscience, New York, 2007, vol. 1
- (2007) The Chemistry of Anilines, Ed.

8
- 36849030278
- E. M. Beccalli G. Broggini M. Martinelli S. Sottocornola Chem. Rev. 2007 107 5318
- (2007) Chem. Rev. , vol.107 , pp. 5318
- Beccalli, E.M.¹ Broggini, G.² Martinelli, M.³ Sottocornola, S.⁴

9
- 34249101833
- C. A. Fleckenstein H. Plenio Organometallics 2007 26 2758
- (2007) Organometallics , vol.26 , pp. 2758
- Fleckenstein, C.A.¹ Plenio, H.²

10
- 33745728743
- S. P. Nolan Chem.-Eur. J. 2006 12 5142
- (2006) Chem.-Eur. J. , vol.12 , pp. 5142
- Nolan, S.P.¹

11
- 33745395707
- J. F. Hartwig Synlett 2006 1283
- (2006) Synlett , pp. 1283
- Hartwig, J.F.¹

12
- 36048987053
- O. Navarro N. Marion J. Mei S. L. Buchwald C. Mauger G. Mignani U. Scholz Adv. Synth. Catal. 2006 348 23
- (2006) Adv. Synth. Catal. , vol.348 , pp. 23
- Navarro, O.¹ Marion, N.² Mei, J.³ Buchwald, S.L.⁴ Mauger, C.⁵ Mignani, G.⁶ Scholz, U.⁷

13
- 14844330054
- For reviews, see:
- Q. Shen S. Shekhar J. P. Stambuli J. F. Hartwig Angew. Chem., Int. Ed. 2005 44 1371
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 1371
- Shen, Q.¹ Shekhar, S.² Stambuli, J.P.³ Hartwig, J.F.⁴

14
- 12344337315
- B. Schlummer U. Scholz Adv. Synth. Catal. 2004 346 1599
- (2004) Adv. Synth. Catal. , vol.346 , pp. 1599
- Schlummer, B.¹ Scholz, U.²

15
- 0003995267
- E.-I. Negishi, Wiley-Interscience, New York, p. 1051
- J. F. Hartwig, in Handbook of Organopalladium Chemistry for Organic Synthesis, ed., E.-I. Negishi,, Wiley-Interscience, New York, 2002, vol. 1, p. 1051
- (2002) Handbook of Organopalladium Chemistry for Organic Synthesis, Ed.
- Hartwig In, J.F.¹

16
- 0008165462
- Copper-catalyzed aminations of aryl halides, see:
- B. H. Yang S. L. Buchwald J. Organomet. Chem. 1999 576 125
- (1999) J. Organomet. Chem. , vol.576 , pp. 125
- Yang, B.H.¹ Buchwald, S.L.²

17
- 33846689629
- M. Taillefer N. Xia N. Ouali Angew. Chem., Int. Ed. 2007 46 934
- (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 934
- Taillefer, M.¹ Xia, N.² Ouali, N.³

18
- 33846195911
- D. Jiang H. Fu Y. Jiang Y. Zhao J. Org. Chem. 2007 72 672
- (2007) J. Org. Chem. , vol.72 , pp. 672
- Jiang, D.¹ Fu, H.² Jiang, Y.³ Zhao, Y.⁴

19
- 33750499990
- X. Guo H. Rao H. Fu Y. Jiang Y. Zhao Adv. Synth. Catal. 2006 348 2197
- (2006) Adv. Synth. Catal. , vol.348 , pp. 2197
- Guo, X.¹ Rao, H.² Fu, H.³ Jiang, Y.⁴ Zhao, Y.⁵

20
- 20844435969
- H. Zhang Q. Qai D. Ma J. Org. Chem. 2005 70 5164
- (2005) J. Org. Chem. , vol.70 , pp. 5164
- Zhang, H.¹ Qai, Q.² Ma, D.³

21
- 9644277114
- I. P. Beletskaya A. V. Cheprakov Coord. Chem. Rev. 2004 248 2337
- (2004) Coord. Chem. Rev. , vol.248 , pp. 2337
- Beletskaya, I.P.¹ Cheprakov, A.V.²

22
- 0345708168
- S. V. Ley A. W. Thomas Angew. Chem., Int. Ed. 2003 42 5400
- (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 5400
- Ley, S.V.¹ Thomas, A.W.²

23
- 36049019584
- D. Hollmann S. Bähn A. Tillack M. Beller Angew. Chem., Int. Ed. 2007 46 8291
- (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 8291
- Hollmann, D.¹ Bähn, S.² Tillack, A.³ Beller, M.⁴

24
- 16244375555
- R. Karvembu R. Prabhakaran N. Natarajan Coord. Chem. Rev. 2005 249 911
- (2005) Coord. Chem. Rev. , vol.249 , pp. 911
- Karvembu, R.¹ Prabhakaran, R.² Natarajan, N.³

25
- 33845375188
- Y. Shvo D. Czarkie Y. Rahamim J. Am. Chem. Soc. 1986 108 740
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 740
- Shvo, Y.¹ Czarkie, D.² Rahamim, Y.³

26
- 37049108518
- Y. Shvo R. M. Laine J. Chem. Soc., Chem. Commun. 1980 753
- (1980) J. Chem. Soc., Chem. Commun. , pp. 753
- Shvo, Y.¹ Laine, R.M.²

27
- 34548191521
- A. Comas-Vives G. Ujaque A. Lledos Organometallics 2007 26 4135
- (2007) Organometallics , vol.26 , pp. 4135
- Comas-Vives, A.¹ Ujaque, G.² Lledos, A.³

28
- 33750702516
- J. S. M. Samec A. H. Ell J. B. Åberg T. Privalov L. Eriksson J.-E. Bäckvall J. Am. Chem. Soc. 2006 128 14293
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 14293
- Samec, J.S.M.¹ Ell, A.H.² Åberg, J.B.³ Privalov, T.⁴ Eriksson, L.⁵ Bäckvall, J.-E.⁶

29
- 33644660116
- J. S. M. Samec J.-E. Bäckvall P. G. Andersson P. Brandt Chem. Soc. Rev. 2006 35 237
- (2006) Chem. Soc. Rev. , vol.35 , pp. 237
- Samec, J.S.M.¹ Bäckvall, J.-E.² Andersson, P.G.³ Brandt, P.⁴

30
- 33745493944
- J. B. Åberg J. S. M. Samec J.-E. Bäckvall Chem. Commun. 2006 2771
- (2006) Chem. Commun. , pp. 2771
- Åberg, J.B.¹ Samec, J.S.M.² Bäckvall, J.-E.³

31
- 26444594290
- C. P. Casey G. A. Bikzhanova Q. Cui I. A. Guzei J. Am. Chem. Soc. 2005 127 14062
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 14062
- Casey, C.P.¹ Bikzhanova, G.A.² Cui, Q.³ Guzei, I.A.⁴

32
- 29244464646
- J. S. M. Samec L. Mony J.-E. Bäckvall Can. J. Chem. 2005 83 909
- (2005) Can. J. Chem. , vol.83 , pp. 909
- Samec, J.S.M.¹ Mony, L.² Bäckvall, J.-E.³

33
- 11144288786
- J. S. M. Samec A. H. Ell J.-E. Bäckvall Chem. Commun. 2004 2748
- (2004) Chem. Commun. , pp. 2748
- Samec, J.S.M.¹ Ell, A.H.² Bäckvall, J.-E.³

34
- 0035857467
- C. P. Casey S. W. Singer D. R. Powell R. K. Hayashi M. Kavana J. Am. Chem. Soc. 2001 123 1090
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 1090
- Casey, C.P.¹ Singer, S.W.² Powell, D.R.³ Hayashi, R.K.⁴ Kavana, M.⁵

35
- 46249088542
- In an ACE-pressure tube under an argon atmosphere the Shvo catalyst (0.02 mmol) and the corresponding alkyl amine (2 mmol of alkyl groups) were dissolved in tert-amyl alcohol (0.5 ml) and aniline (4 mmol). The pressure tube was fitted with a Teflon cap and heated at 150°C for 24 h. The solvent was removed in vacuo, and the crude alkyl aryl amine product was easily purified by column chromatography with pentane-ethyl acetate (20: 1) For an excellent review of the hydrogen borrowing methodology, see:
- In an ACE-pressure tube under an argon atmosphere the Shvo catalyst (0.02 mmol) and the corresponding alkyl amine (2 mmol of alkyl groups) were dissolved in tert-amyl alcohol (0.5 ml) and aniline (4 mmol). The pressure tube was fitted with a Teflon cap and heated at 150°C for 24 h. The solvent was removed in vacuo, and the crude alkyl aryl amine product was easily purified by column chromatography with pentane-ethyl acetate (20: 1)

36
- 34547158082
- Similar observations have been made in the amination of alcohols:
- M. H. S. A. Hamid P. A. Slatford J. M. J. Williams Adv. Synth. Catal. 2007 349 1555
- (2007) Adv. Synth. Catal. , vol.349 , pp. 1555
- Hamid, M.H.S.A.¹ Slatford, P.A.² Williams, J.M.J.³

37
- 34248151386
- D. Hollmann A. Tillack D. Michalik R. Jackstell M. Beller Chem.-Asian J. 2007 3 403
- (2007) Chem.-Asian J. , vol.3 , pp. 403
- Hollmann, D.¹ Tillack, A.² Michalik, D.³ Jackstell, R.⁴ Beller, M.⁵

38
- 33750618390
- A. Tillack D. Hollmann D. Michalik M. Beller Tetrahedron Lett. 2006 47 8881
- (2006) Tetrahedron Lett. , vol.47 , pp. 8881
- Tillack, A.¹ Hollmann, D.² Michalik, D.³ Beller, M.⁴

39
- 33846903549
- M. H. S. A. Hamid J. M. J. Williams Chem. Commun. 2007 725
- (2007) Chem. Commun. , pp. 725
- Hamid, M.H.S.A.¹ Williams, J.M.J.²

40
- 12444281012
- G. Cami-Kobeci P. A. Slatford M. K. Whittlesey J. M. J. Williams Bioorg. Med. Chem. Lett. 2005 15 535
- (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 535
- Cami-Kobeci, G.¹ Slatford, P.A.² Whittlesey, M.K.³ Williams, J.M.J.⁴

41
- 31444447801
- A. Miyazawa K. Saitou K. Tanaka T. M. Gädda M. Tashiro G. K. S. Prakash G. L. Olah Tetrahedron Lett. 2006 47 1437
- (2006) Tetrahedron Lett. , vol.47 , pp. 1437
- Miyazawa, A.¹ Saitou, K.² Tanaka, K.³ Gädda, T.M.⁴ Tashiro, M.⁵ Prakash, G.K.S.⁶ Olah, G.L.⁷

42
- 0000575377
- C. W. Jung J. D. Fellmann P. E. Garrou Organometallics 1983 2 1042
- (1983) Organometallics , vol.2 , pp. 1042
- Jung, C.W.¹ Fellmann, J.D.² Garrou, P.E.³

43
- 34247582709
- J. J. Li Z. Wang L. H. Mitchell J. Org. Chem. 2007 72 3606
- (2007) J. Org. Chem. , vol.72 , pp. 3606
- Li, J.J.¹ Wang, Z.² Mitchell, L.H.³

44
- 29144502450
- M. Kreis C. J. Friedmann S. Braese Chem.-Eur. J. 2005 11 7387
- (2005) Chem.-Eur. J. , vol.11 , pp. 7387
- Kreis, M.¹ Friedmann, C.J.² Braese, S.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.