Evidence for the role of tetramethylethylenediamine in aqueous negishi cross-coupling: Synthesis of nonproteinogenic phenylalanine derivatives on water

Journal of Organic Chemistry

Volumn 76, Issue 6, 2011, Pages 1727-1734

  Ross, Andrew J ^a   Dreiocker, Frank ^b   Schä Fer, Mathias ^b   Oomens, Jos ^c,d   Meijer, Anthony J H M ^a   Pickup, Barry T ^a   Jackson, Richard F W ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b UNIVERSITY OF COLOGNE   (Germany)

^c FOM INSTITUTE FOR PLASMA PHYSICS RIJNHUIZEN   (Netherlands)

^d UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLZINC HALIDES; AQUEOUS CONDITION; ARYL IODIDES; BOC GROUP; CARBONYL GROUPS; CLUSTER CATIONS; DFT CALCULATION; GASPHASE; HIGH-LEVEL DFT; INFRARED MULTIPHOTON DISSOCIATION; INTERNAL COORDINATION; IR SPECTRUM; LOW ENERGIES; NEGISHI CROSS-COUPLING; PCM MODEL; REDUCTIVE DIMERIZATION; ROOM TEMPERATURE; STABILIZING INTERACTIONS; TANDEM MASS SPECTROMETRY; TETRAMETHYLETHYLENEDIAMINE; WATER SOLVENTS; ZINC ATOMS;

AMINO ACIDS; IODINE; IONIZATION OF GASES; IONIZATION OF LIQUIDS; MASS SPECTROMETRY; ORGANOMETALLICS; POSITIVE IONS; SYNTHESIS (CHEMICAL);

ZINC;

CARBONYL DERIVATIVE; ETHYLENE DERIVATIVE; IODIDE; IODINE; METHYL 2 (TERT BUTOXYCARBONYLAMINO) 3 (3 CHLORO 4 FLUOROPHENYL)PROPANOATE; METHYL 2 (TERT BUTOXYCARBONYLAMINO) 3 (3 CHLOROPHENYL)PROPANOATE; METHYL 2 (TERT BUTOXYCARBONYLAMINO) 3 (3,4 DIFLUOROPHENYL)PROPANOATE; METHYL 2 (TERT BUTOXYCARBONYLAMINO) 3 (3,5 DIFLUOROPHENYL)PROPANOATE; METHYL 2 (TERT BUTOXYCARBONYLAMINO) 3 [3 (TRIFLUOROMETHYL)PHENYL]PROPANOATE; METHYL 2 (TERT BUTOXYCARBONYLAMINO) 3 [4 (TRIFLUOROMETHYL)PHENYL]PROPANOATE; N,N,N',N' TETRAMETHYLETHYLENEDIAMINE; PHENYLALANINE DERIVATIVE; UNCLASSIFIED DRUG; WATER; ZINC;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; DIMERIZATION; INFRARED SPECTROSCOPY; IONIZATION; ROOM TEMPERATURE; SYNTHESIS; TANDEM MASS SPECTROMETRY;

ETHYLENEDIAMINES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHENYLALANINE; THERMODYNAMICS; WATER;

EID: 79953867737     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102334c     Document Type: Article

References (34)

1. Dreiocker, F.; Oomens, J.; Meijer, A. J. H. M.; Pickup, B. T.; Jackson, R. F. W.; Schä fer, M. J. Org. Chem. 2010, 75, 1203-1213.
2. Polfer, N. C.; Oomens, J. Mass Spectrom. Rev. 2009, 28, 468-494.
3. MacAleese, L.; Maitre, P. Mass Spectrom. Rev. 2007, 26, 583-605.
4. Fleckenstein, J. E.; Koszinowski, K. Chem.-Eur. J. 2009, 15, 12745-12753.
5. Koszinowski, K.; Böhrer, P. Organometallics 2009, 28, 771-779.
6. Koszinowski, K.; Böhrer, P. Organometallics 2009, 28, 100-110.
7. Di Marco, V. B.; Bombi, G. G. Mass Spectrom. Rev. 2006, 25, 347-379.
8. Caggiano, L.; Jackson, R. F. W.; Meijer, A.; Pickup, B. T.; Wilkinson, K. A. Chem.-Eur. J. 2008, 14, 8798-8802.
9. Krasovskiy, A.; Duplais, C.; Lipshutz, B. H. J. Am. Chem. Soc. 2009, 131, 15592-15593.
10. Duplais, C.; Krasovskiy, A.; Wattenberg, A.; Lipshutz, B. H. Chem. Commun 2010, 46, 562-564.
11. Lipshutz, B. H.; Abela, A. R.; Boskovic, Z. V.; Nishikata, T.; Duplais, C.; Krasovskiy, A. Top. Catal. 2010, 53, 985-990.
12. Rilatt, I.; Caggiano, L.; Jackson, R. F.W. Synlett 2005, 2701-2719.
13. Ross, A. J.; Lang, H. L.; Jackson, R. F. W. J. Org. Chem. 2010, 75, 245-248.
14. Chalker, J. M.; Wood, C. S. C.; Davis, B. G. J. Am. Chem. Soc. 2009, 131, 16346-16347.
15. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553-566.
16. Irikura, K. K.; Johnson, R. D.; Kacker, R. N. J. Phys. Chem. A 2005, 109, 8430-8437.
17. Foresman, J. B.; Frisch, A. E. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian, Inc.: Pittsburgh, PA, 1996.
18. Bythell, B. J.; Dain, R. P.; Curtice, S. S.; Oomens, J.; Steill, J. D.; Groenewold, G. S.; Paizs, B.; Van, S. M. J. J. Phys. Chem. A 2010, 114, 5076-5082.
19. Lemaire, J.; Boissel, P.; Heninger, M.; Mauclaire, G.; Bellec, G.; Mestdagh, H.; Simon, A.; Le, C. S.; Ortega, J. M.; Glotin, F.; Maitre, P. Phys. Rev. Lett. 2002, 89, 273002/1-273002/4.
20. Drayss, M. K.; Blunk, D.; Oomens, J.; Gao, B.; Wyttenbach, T.; Bowers, M. T.; Schäfer, M. J. Phys. Chem. A 2009, 113, 9543-9550.
21. Asmis, K. R.; Pivonka, N. L.; Santambrogio, G.; Brummer, M.; Kaposta, C.; Neumark, D. M.; Woste, L. Science 2003, 299, 1375-7.
22. Oomens, J.; Tielens, A. G. G. M.; Sartakov, B. G.; von, H. G.; Meijer, G. Astrophys. J. 2003, 591, 968-985.
23. Polfer, N. C.; Oomens, J.; Moore, D. T.; Von, H. G.; Meijer, G.; Dunbar, R. C. J. Am. Chem. Soc. 2006, 128, 517-525.
24. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian, Inc.: Wallingford, CT, 2009.
25. Jackson, R. F. W.; Moore, R. J.; Dexter, C. S.; Elliot, J.; Mowbray, C. E. J. Org. Chem. 1998, 63, 7875-7884.
26. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456-463.
27. Jackson, R. F. W.; Rilatt, I.; Murray, P. J. Org. Biomol. Chem. 2003, 2, 110-113.
28. Oepts, D.; Vandermeer, A. F. G.; Vanamersfoort, P. W. Infrared Phys. Technol. 1995, 36, 297-308.
29. Polfer, N. C.; Oomens, J. Phys. Chem. Chem. Phys. 2007, 9, 3804-3817.
30. Valle, J. J.; Eyler, J. R.; Oomens, J.; Moore, D. T.; van der Meer, A. F. G.; von Helden, G.; Meijer, G.; Hendrickson, C. L.; Marshall, A. G.; Blakney, G. T. Rev. Sci. Instrum. 2005, 76, 023103.
31. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
32. Nicklass, A.; Dolg, M.; Stoll, H.; Preuss, H. J. Chem. Phys. 1995, 102, 8942-8952.
33. Cao, X. Y.; Dolg, M. J. Chem. Phys. 2001, 115, 7348-7355.
34. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3093.