Ritter-type amidation of alkylboron derivatives with nitriles

Tetrahedron Letters

Volumn 50, Issue 49, 2009, Pages 6855-6857

  Cazorla, Clément ^a   Métay, Estelle ^a   Andrioletti, Bruno ^a   Lemaire, Marc ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

Alkylboronic; Copper; Oxidative nucleophilic substitution; Ritter amidation

Indexed keywords

1 PHENYLETHYLBORONATE; 2 PHENYLVINYLBORONIC ACID; 4 BROMOACETONITRILE; 4 NITROBENZONITRILE; ACETONITRILE; AMIDE; BENZONITRILE; BORON DERIVATIVE; BORON TRIFLUORIDE DIETHYL ETHERATE; COPPER ACETATE; ETHER DERIVATIVE; N (1 PHENYLETHYL)ACETAMIDE; NITRILE; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; GAS CHROMATOGRAPHY; HYDROLYSIS; OXIDATION; ROOM TEMPERATURE; STOICHIOMETRY; SYNTHESIS;

EID: 70350092754     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.132     Document Type: Article

References (23)

1. Ritter J.J., and Kalish J. J. Am. Chem. Soc. 70 (1948) 4048-4050
2. Ritter J.J. J. Am. Chem. Soc. 70 (1948) 4045-4048
3. Kacan M., and McKillop A. Synth. Commun. 23 (1993) 2185-2189
4. Welniak M. Pol. J. Chem. 76 (2002) 1405-1411
5. Dos Santos M., Crousse B., and Bonnet-Delpon D. Tetrahedron Lett. 50 (2009) 857-859
6. Jirgensons A., Kauss V., Kalvinsh I., and Gold M.R.A. Synthesis (2000) 1709-1712
7. Callens E., Burton A.J., and Barret A.G.M. Tetrahedron Lett. 47 (2006) 8699-8701
8. Anxionnat B., Guérinot A., Reymond S., and Cossy J. Tetrahedron Lett. 50 (2009) 3470-3473
9. Concellón J.M., Suárez J.R., and del Solar V. J. Org. Chem. 70 (2005) 7447-7450
10. Senanayake C.H., Larsen R.D., DiMichele L.M., Liu L., Toma P.H., Ball R.G., Verhoeven T.R., and Reider P.J. Tetrahedron: Asymmetry 7 (1995) 1501-1506
11. Martin R., and Buchwald S.L. Acc. Chem. Res. 41 (2008) 1461-1473
12. Doucet H. Eur. J. Org. Chem. 12 (2008) 2013-2030
13. Molander G.A., and Ellis N. Acc. Chem. Res. 40 (2007) 275-286
14. Hayashi T., and Yamasaki K. Chem. Rev. 103 (2003) 2829-2844
15. Sakuma S., and Miyaura N. J. Org. Chem. 66 (2001) 8944-8946
16. Darses S., and Genet J.-P. Chem. Rev. 108 (2008) 288-325
17. Hayashi T. Synlett (2001) 879-887
18. Sörgel S., Tokunaga N., Sasaki K., Okamoto K., and Hayashi T. Org. Lett. 10 (2008) 589-592
19. Molander G.A., Gormisky P.E., and Sandrock D.L. J. Org. Chem. 73 (2008) 2052-2057
20. Molander G.A., and Ham J. Org. Lett. 8 (2006) 2031-2034
21. Cazorla C., Métay E., Andrioletti B., and Lemaire M. Tetrahedron Lett. 50 (2009) 3936-3938
22. Kürti L., and Czakó B. Strategic Applications of Named Reactions in Organic Synthesis (2005), Elsevier Academic Press, San Diego pp 382-383
23. Bardin V.V., Adonin N.Y., and Frohn H.J. J. Fluorine Chem. 128 (2007) 699-702