A lactam-derived vinyl boronate as a stable and crystalline reagent for the synthesis of 2-substituted piperidines by Pd-catalyzed coupling reactions

Tetrahedron Letters

Volumn 45, Issue 27, 2004, Pages 5271-5274

  Ferrali, Alessandro ^a   Guarna, Antonio ^a   Lo Galbo, Fabrizio ^a   Occhiato, Ernesto G ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Boronates; Coupling; Lactams; Palladium; Piperidines; Triflates

Indexed keywords

2 PIPERIDONE; BORONIC ACID DERIVATIVE; LACTAM; PALLADIUM; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG; VINYL BORONATE;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; DRUG SYNTHESIS; SUBSTITUTION REACTION;

EID: 2942609781     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.015     Document Type: Article

References (28)

1. For a review on the chemistry of lactam-derived vinyl triflates see: Occhiato E.G. Mini-Rev. Org. Chem. 1:2004;149
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15. Bis(pinacolato)diboron 3 can also be prepared according to the procedure reported in: Abu Ali H.A., Goldberg I., Srebnik M. Eur. J. Inorg. Chem. 2002;73
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21. 2 according to a procedure reported in Ref. 2a
22. +, 0.1), 194 (20), 152 (31), 91 (100). Elemental analysis calcd C, 66.49; H, 7.64; N, 4.08. Found C, 66.84; H, 7.74; N, 4.01
23. 3) spectrum of 5: δ 7.35-7.25 (m, 10H), 5.33 (br t, 2H), 5.07 (s, 4H), 3.50-3.10 (br m, 4H), 2.10-1.95 (br m, 4H), 1.75-1.50 (br m, 4H)
24. Attempts at preparing the corresponding vinyl boronate from the N-Ts pyrrolidinone-derived vinyl triflate were hampered by the ready decomposition of this intermediate under the coupling conditions
25. This palladacycle was prepared according to the procedure reported in: Herrmann W.A., Brossmer K.Ö., Reisinger C.-P., Priermeier T., Beller M., Fischer H. Angew. Chem., Int. Ed. Engl. 34:1995;1844
26. 2e (33 mg, 75%) as a colorless oil
27. 2e (39 mg, 88%) as a colorless oil
28. The reaction takes also place at lower temperature (90°C) with the Herrmann catalyst, although it is much slower (15% conversion after 3.5 h) and, in practice, the ratio between 9 and by-product 7 does not change