Ni-catalyzed α-arylation of secondary α-bromo-α-fluoro- β-lactam: Cross-coupling of a secondary fluorine-containing electrophile

Tetrahedron

Volumn 69, Issue 5, 2013, Pages 1559-1565

  Tarui, Atsushi ^a   Kondo, Shoji ^a   Sato, Kazuyuki ^a   Omote, Masaaki ^a   Minami, Hideki ^b   Miwa, Yoshihisa ^b   Ando, Akira ^a  

^a SETSUNAN UNIVERSITY   (Japan)

^b HIROSHIMA INTERNATIONAL UNIVERSITY   (Japan)

Author keywords

Cross coupling; Diastereoselective; Fluorine; Fluoro lactam; Kumada reaction

Indexed keywords

2,2' ISOPROPYLIDENE BIS(4 PHENYL 2 OXAZOLINE); ALPHA BROMO ALPHA FLUORO BETA LACTAM; ANTI 1 BENZYL 3 (3 CHLOROPHENYL) 3 FLUORO 4 PHENYLAZETIDIN 2 ONE; ANTI 1 BENZYL 3 (4 CHLOROPHENYL) 3 FLUORO 4 PHENYLAZETIDIN 2 ONE; ANTI 1 BENZYL 3 FLUORO 3 (1 METHYL 1H INDOL 5 YL) 4 PHENYLAZETIDIN 2ONE; ANTI 1 BENZYL 3 FLUORO 3 (3 METHOXYPHENYL) 4 PHENYLAZETIDIN 2 ONE; ANTI 1 BENZYL 3 FLUORO 3 (3 METHYLPHENYL) 4 PHENYAZETIDIN 2 ONE; ANTI 1 BENZYL 3 FLUORO 3 (4 METHOXYPHENYL) 4 PHENYLAZETIDIN 2 ONE; ANTI 1 BENZYL 3 FLUORO 3 (4 METHYLPHENYL) 4 PHENYAZETIDIN 2 ONE; ANTI 1 BENZYL 3 FLUORO 3 (NAPHTHALEN 1 YL) 4 PHENYLAZETIDIN 2 ONE; ANTI 1 BENZYL 3 FLUORO 3 (NAPHTHALEN 2 YL) 4 PHENYLAZETIDIN 2 ONE; ANTI 1 BENZYL 3 FLUORO 3 [3,4 (METHYLENEDIOXY)PHENYL] 4 PHENYLAZETIDIN 2 ONE; ANTI 1 BENZYL 3 FLUORO 3,4 DIPHENYLAZETIDIN 2 ONE; ANTI 1 BENZYL 3 FLUORO 4 PHENYL 3 [3 (TRIFLUOROMETHYL)PHENYL]AZETIDIN 2 ONE; ANTI 1 BENZYL 3 FLUORO 4 PHENYL 3 [4 (TRIFLUOROMETHYL)PHENYL]AZETIDINE 2 ONE; ANTI 3 (BENZOFURAN 5 YL) 1 BENZYL 3 FLUORO 4 PHENYLAZETIDIN 2 ONE; ANTI 3 FLUORO 1 (4 METHOXYBENZYL) 3,4 DIPHENYLAZETIDIN 2 ONE; ANTI 3 FLUORO 1,3,4 TRIPHENYLAZETIDIN 2 ONE; ANTI 3 FLUORO 3,4 DIPHENYLAZETIDIN 2 ONE; BETA LACTAM ANTIBIOTIC; BIS(OXAZOLINE); ELECTROPHILE; FLUORINE; GRIGNARD REAGENT; NICKEL; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ALPHA ARYLATION; ARTICLE; ARYLATION; CATALYSIS; CONTROLLED STUDY; CROSS COUPLING REACTION; DEPROTECTION REACTION; ISOMER; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 84872119883     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.12.002     Document Type: Article

References (28)

1. A. Nangia, K. Biradha, and G.R. Desiraju J. Chem. Soc., Perkin Trans. 2 1996 943 953
2. C.C. Martel, A. Amoroso, E.C.Y. Woon, A. Zervosen, S. Inglis, A. Martins, O. Verlaine, A.M. Rydzik, V. Job, A. Luxen, B. Joris, C.J. Schofield, and A. Dessen ACS Chem. Biol. 6 2011 943 951
3. P. Galletti, and D. Giacomini Curr. Med. Chem. 18 2011 4265 4283
4. K.L. Kirk Org. Process Res. Dev. 12 2008 305 321
5. S. Purser, P.R. Moore, S. Swallow, and V. Gouverneur Chem. Soc. Rev. 37 2008 320 330
6. D. O'Hagan J. Fluorine Chem. 131 2010 1071 1081
7. J.T. Welch, K. Araki, R. Kawecki, and J.A. Wichtowski J. Org. Chem. 58 1993 2454 2462
8. R. Kawecki, and J.T. Welch Tetrahedron Lett. 34 1993 3087 3090
9. D.S. Reddy, N. Shibata, J. Nagai, S. Nakamura, T. Toru, and S. Kanemasa Angew. Chem., Int. Ed. 47 2008 164 168
10. R.J.P. Corriu, and J.P. Masse J. Chem. Soc., Chem. Commun. 1972 144
11. K. Tamao, K. Sumitani, and M. Kumada J. Am. Chem. Soc. 94 1972 4374 4376
12. P. Liu, and E.N. Jacobsen J. Am. Chem. Soc. 123 2001 10772 10773
13. T. Banno, Y. Hayakawa, and M. Umeno J. Organomet. Chem. 653 2002 288 291
14. A. Fürstner, A. Leitner, M. Méndez, and H. Krause J. Am. Chem. Soc. 124 2002 13856 13863
15. L. Ackermann, and A. Althammer Org. Lett. 8 2006 3457 3460
16. R. Martin, and S.L. Buchwald J. Am. Chem. Soc. 129 2007 3844 3845
17. S. Lou, and G.C. Fu J. Am. Chem. Soc. 132 2010 1264 1266
18. For Suzuki coupling: P.M. Ludin, and G.C. Fu J. Am. Chem. Soc. 132 2010 11027 11029
19. For Negishi coupling: C. Fischer, and G.C. Fu J. Am. Chem. Soc. 127 2005 4594 4595
20. S. Ge, and J.F. Hartwig J. Am. Chem. Soc. 133 2011 16330 16333
21. C. Liu, C. He, W. Shi, M. Chen, and A. Lei Org. Lett. 9 2007 5601 5604
22. T. Hama, X. Liu, D.A. Culkin, and J.F. Hartwig J. Am. Chem. Soc. 125 2003 11176 11177
23. A. Tarui, N. Kawashima, K. Sato, M. Omote, Y. Miwa, H. Minami, and A. Ando Tetrahedron Lett. 51 2010 2000 2003
24. S. Tasler, and B.H. Lipshutz J. Org. Chem. 68 2003 1190 1199
25. CCDC 898418 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
26. Generally, the anti vicinal coupling constant value for small cyclic compounds (3 or 4 membered rings) is smaller than syn value. This also applies to vicinal H-F coupling constants. The vicinal H-F coupling constant of 2a was 3.5 Hz. The vicinal H-F coupling constant on small cyclic rings is described in the following book: W.R. Dorbier Jr. Guide to Fluorine NMR for Organic Chemist 2009 John Wiley & Sons New Jersey pp 46-47
27. L. Miao, I. Haque, M.R. Manzoni, W.S. Tham, and S.R. Chemler Org. Lett. 12 2010 4739 4741
28. H.-S. Lin, and L.A. Paquette Synth. Commun. 24 1994 2503 2506