Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles

Organic Letters

Volumn 6, Issue 14, 2004, Pages 2405-2408

  He, Ling ^a   Chan, Philip Wai Hong ^a   Tsui, Wai Man ^a   Yu, Wing Yiu ^a   Che, Chi Ming ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

RUTHENIUM;

AMIDATION; AMINATION; ARTICLE; CATALYSIS; CATALYST; MOLECULAR INTERACTION; REACTION ANALYSIS; SUBSTITUTION REACTION; ULTRASOUND;

EID: 3242735140     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049232j     Document Type: Article

References (24)

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17. Selected examples: (a) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (b) Reymond, J. L.; Pinkerton, A. A.; Vogel, P. J. Org. Chem. 1991, 56, 2128. (c) Bossio, R.; Marcaccini, S.; Pepino, R.; Torroba, T. J. Org. Chem. 1996, 61, 2202. (d) Marcotte, F.-A.; Rombouts, F. J. R.; Lubell, W. D. J. Org. Chem. 2003, 68, 6984.
18. Selected examples: (a) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (b) Reymond, J. L.; Pinkerton, A. A.; Vogel, P. J. Org. Chem. 1991, 56, 2128. (c) Bossio, R.; Marcaccini, S.; Pepino, R.; Torroba, T. J. Org. Chem. 1996, 61, 2202. (d) Marcotte, F.-A.; Rombouts, F. J. R.; Lubell, W. D. J. Org. Chem. 2003, 68, 6984.
19. Selected examples: (a) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (b) Reymond, J. L.; Pinkerton, A. A.; Vogel, P. J. Org. Chem. 1991, 56, 2128. (c) Bossio, R.; Marcaccini, S.; Pepino, R.; Torroba, T. J. Org. Chem. 1996, 61, 2202. (d) Marcotte, F.-A.; Rombouts, F. J. R.; Lubell, W. D. J. Org. Chem. 2003, 68, 6984.
20. Selected examples: (a) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (b) Reymond, J. L.; Pinkerton, A. A.; Vogel, P. J. Org. Chem. 1991, 56, 2128. (c) Bossio, R.; Marcaccini, S.; Pepino, R.; Torroba, T. J. Org. Chem. 1996, 61, 2202. (d) Marcotte, F.-A.; Rombouts, F. J. R.; Lubell, W. D. J. Org. Chem. 2003, 68, 6984.
21. Amount of 4 Å molecular sieves employed is equivalent to the amount (by mass) of PhI=NTs used.
22. See Supporting Information for full experimental details.
23. See Supporting Information. Also, CCDC 219719-219720 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk).
24. 2 or benyzl peroxide as an additive were found to give similar outcomes (i.e., reduction of Ru(VI) to Ru(IV) with no amidation product detected). Also, see Supporting Information for experimental details.