Oxidative alkynylation of imines with alkynylcopper reagents: A straightforward and practical entry to ynimines

Synthesis

Volumn 44, Issue 10, 2012, Pages 1491-1500

  Laouiti, Anouar ^a,b   Jouvin, Kvin ^a   Bourdreux, Flavien ^a   Rammah, Mohamedm ^b   Rammah, Mohamedb ^b   Evano, Gwilherm ^a,c  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

^b UNIVERSITY OF MONASTIR   (Tunisia)

^c UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

Author keywords

alkynes; copper; cross coupling; imines; organometallic reagents; oxidation

Indexed keywords

ALKYNES; ALKYNYL GROUPS; ALKYNYLATIONS; CROSS-COUPLINGS; IMINES; KETIMINES; ORGANOMETALLIC REAGENT; POLYMERIC COMPOUNDS; ROOM TEMPERATURE;

ACETYLENE; COPPER; ORGANOMETALLICS; OXIDATION;

NITROGEN COMPOUNDS;

ALKYLNYLCOPPER; ALKYNYL GROUP; COPPER DERIVATIVE; CRYSTALLIN; DIMETHYLIMIDAZOLE; IMIDAZOLE DERIVATIVE; IMINE; KETIMINE DERIVATIVE; N (DIPHENYLMETHYLENE)OCT 1 YN 1 AMINE; N (DIPHENYLMETHYLENE)PENT 1 YN 1 AMINE; N (PHENYLPENTYLIDENE)OCT 1 YN 1 AMINE; N (PHENYLPENTYLIDENE)PENT 1 YN 1 AMINE; N [1 (2 CHLOROPHENYL)PENTYLIDENE]OCT 1 YN 1 AMINE; N [1 (2 CHLOROPHENYL)PENTYLIDENE]PENT 1 YN 1 AMINE; N [1 (2 METHOXYPHENYL)PENTYLIDENE]OCT 1 YN 1 AMINE; N [1 (2 METHOXYPHENYL)PENTYLIDENE]PENT 1 YN 1 AMINE; N [1 (2 TOLYL)ETHYLIDENE]PENT 1 YN 1 AMINE; N [1 (2 TOLYL)PENTYLIDENE]OCT 1 YN 1 AMINE; N [1 (2 TOLYL)PENTYLIDENE]PENT 1 YN 1 AMINE; N [1 (2,3 DIMETHYLPHENYL)PENTYLIDENE]OCTYN 1 YN 1 AMINE; N [1 (2,3 DIMETHYLPHENYL)PENTYLIDENE]PENTYN 1 YN 1 AMINE; N [1 (NAPHTHALEN 1 YL)PENTYLIDENE]OCT 1 YN 1 AMINE; N [1 (NAPHTHALEN 1 YL)PENTYLIDENE]PENT 1 YN 1 AMINE; N [1 (NAPHTHALEN 2 YL)PENTYLIDENE]OCT 1 YN 1 AMINE; N [1 (NAPHTHALEN 2 YL)PENTYLIDENE]PENT 1 YN 1 AMINE; N [PHENYL(2 TOLYL)METHYLENE]OCT 1 YN 1 AMINE; N [PHENYL(2 TOLYL)METHYLENE]PENT 1 YN 1 AMINE; OXYGEN; UNCLASSIFIED DRUG; YNIMINE DERIVATIVE;

ADDITION REACTION; ALKYNYLATION; ARTICLE; CATALYST; CHEMICAL INTERACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CRYSTAL STRUCTURE; MOLECULAR STABILITY; OXIDATIVE ALKYNYLATION; POLYMERIZATION; ROOM TEMPERATURE; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 84859545785     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289760     Document Type: Article

References (31)

1. Glaser C. Justus Liebigs Ann. Chem.: 1870; 154 137
2. Nast R, Pfab W. Chem. Ber.: 1956; 89 415
3. Blake D, Calvin G, Coates GE. Proc. Chem. Soc., London: 1959; 396
4. Sazonova VA, Ya NK. Zh. Obshch. Khim.: 1956; 26 1876; Chem. Abstr. 1957, 51, 4981c
5. Stephens RD, Castro CE. J. Org. Chem.: 1963; 28 3313
6. Atkinson RE, Curtis RF, Taylor JA. J. Chem. Soc. C: 1967; 578
7. Owsley DC, Castro CE. Org. Synth. Coll. Vol. VI. John Wiley & Sons London: 1988; 916
8. Ito H, Arimoto K, Sensui H.-o, Hosomi A. Tetrahedron Lett.: 1997; 38 3977
9. Chui SS. Y, Ng MF. Y, Che C.-M. Chem.-Eur. J.: 2005; 11 1739
10. Buckley BR, Dann SE, Harris DP, Heanay H, Stubbs EC. Chem. Commun.: 2010; 46 2274
11. Surry DS, Spring DA. Chem. Soc. Rev.: 2006; 35 218
12. Aves SJ, Spring DR. The Chemistry of Functional Groups. In The Chemistry of Organocopper Compounds Vol. 24 Rappoport Z, Marek I. John Wiley & Sons Ltd Chichester: 2009; 585
13. Alberti A, Can F, Dembech P, Lazzari D, Ricci A, Seconi G. J. Org. Chem.: 1996; 61 1677
14. Can F, Brancaleoni D, Dembech P, Ricci A, Seconi G. Synthesis: 1997; 545
15. del Amo V, Dubbaka SR, Krasovskiy A, Knochel P. Angew. Chem. Int. Ed.: 2006; 45 7838
16. Boudet N, Dubbaka SR, Knochel P. Org. Lett.: 2008; 10 1715
17. Kienle M, Dubbaka SR, del Amo V, Knochel P. Synthesis: 2007; 1272
18. Kienle M, Dunst C, Knochel P. Org. Lett.: 2009; 11 5158
19. Coste A, Karthikeyan G, Couty F, Evano G. Angew. Chem. Int. Ed.: 2009; 48 4381
20. Coste A, Couty F, Evano G. Org. Lett.: 2009; 11 4454
21. Jouvin K, Couty F, Evano G. Org. Lett.: 2010; 12 3272
22. Jouvin K, Evano G. Chim. Oggi: 2011; 29 31
23. Fadel A, Legrand F, Evano G, Rabasso N. Adv. Synth. Catal.: 2011; 353 263
24. Laouiti A, Rammah MM, Rammah MB, Marrot J, Couty F, Evano G. Org. Lett.: 2012; 14 6
25. Evano G, Coste A, Jouvin K. Angew. Chem. Int. Ed.: 2010; 49 2840
26. DeKorver KA, Li H, Lohse AG, Hayashi R, Lu Z, Zhang Y, Hsung RP. Chem. Rev.: 2010; 110 5064
27. David WM, Kerwin SM. J. Am. Chem. Soc.: 1997; 119 1464
28. Hoffner J, Schottelius MJ, Feichtinger D, Chen P. J. Am. Chem. Soc.: 1998; 120 376
29. Feng L, Kumar D, Kerwin SM. J. Org. Chem.: 2003; 68 2234
30. Feng L, Kerwin SM. Tetrahedron Lett.: 2003; 44 3463
31. Feng L, Zhang A, Kerwin SM. Org. Lett.: 2006; 8 1983