ScienceDirect - Tetrahedron Letters : Palladium(O) catalyzed azidation and amination of allyl acetates. Selective synthesis of allyl azides and primary allylamines

Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 227-230

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doi:10.1016/S0040-4039(00)83983-0

Palladium(O) catalyzed azidation and amination of allyl acetates. Selective synthesis of allyl azides and primary allylamines

Shun-Ichi Murahashi, ^*, Yoshio Tanigawa, Yasushi Imada and Yuki Taniguchi

Department of Chemistry, Faculty of Engineering Science, Osaka University, Machikaneyama, Toyonaka, Osaka, 560, Japan

Received 7 November 1985.

Available online 8 March 2001.

Abstract

Palladium catalyzed reaction of allyl acetates with azide ion gives allyl azides, which are readily converted into the corresponding primary allylamines upon treatment with PPh₃/NaOH.

References

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Y. Tanigawa, K Nishimura, A. Kawasaki and S.-I. Murahashi Tetrahedron Lett. (1982), p. 5549. Abstract | PDF (237 K) | View Record in Scopus | Cited By in Scopus (31)
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B.M. Trost, S.A. Godleski and J.P. Genét J. Am. Chem. Soc. 100 (1978), p. 3930. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (42)
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Soft nucleophiles attack at the carbon of π-allyl palladium complexes (ref 1), while hard nucleophiles attack at palladium atom. See ref 1 and also: S.A. Stanton, S.W. Felman, C.S. Parkhurst and S.A. Godleski J. Am. Chem. Soc. 105 (1983), p. 1964. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (31)

These results are explained by syn-anti isomerisation of π-allylpalladium intermediate before the nucleophilic attack^2,7a.

A. Gagneux, S. Winstein and W.G. Young J. Am. Chem. Soc. 82 (1960), p. 5956. Full Text via CrossRef

¹H NMR (CDCl₃) δ 2.38 (d, J=4.3 Hz, 2H), 2.78 (t, J=4.3 Hz, 2H), 3.16 (d, J=5.0 Hz, 2H), 3.62 (s, 2H), 3.73 (d, J=5.0 Hz, 2H), 5.71 (dt, J=15.3 and 5.0 Hz, 1H), 5.75 (dt, J=15.3 and 5.0 Hz, 1H), 7.05–7.40 (m, 5H); mass spectrum m/e 255 (M⁺).

M. Vaultier, N. Knouzi and R. Carrié Tetrahedron Lett. (1983), p. 763 and references cited therein . Abstract | PDF (116 K) | View Record in Scopus | Cited By in Scopus (139)

¹H NMR (CDCl₃) δ 1.07 (d, J=7.0 Hz, 3H), 1.14–1.85 (m, 9H), 1.85–2.45 (m, 2H), 2.67–3.06 (m, 2H), 3.14–3.47 (m, 2H), 5.64 (dt, J=16.0 and 4.7 Hz, 1H), 5.65 (dt, J=16.0 and 4.7 Hz, 1H); mass spectrum m/e 168 (M⁺).

E.J. Corey, K.C. Nicolaou, R.D. Balanson and Y. Machida Synthesis (1975), p. 590. Full Text via CrossRef
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J. Garcia, F. Urpi and J. Vilarrasa Tetrahedron Lett. (1984), p. 4841. Abstract | PDF (273 K) | View Record in Scopus | Cited By in Scopus (49)

P.H. Lambert, M. Vaultier and R.J. Carrié Chem. Soc. (1982), p. 1224 Chem. Commun. . Full Text via CrossRef
O. Tsuge, S. Kanamasa and K. Matsuda J. Org. Chem. 49 (1984), p. 2688. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (15)

E.J. Corey, B. Samuelsson and F.A. Luzzio J. Am. Chem. Soc. 106 (1984), p. 3682. Full Text via CrossRef

Y. Tanigawa, H. Ohta, A. Sonoda and S.-I. Murahashi J. Am. Chem. Soc. 100 (1978), p. 4610. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (5)

Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 227-230

Result list | previous < 27 of 36 > next

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