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Sukzessive Reaktion von Bis(iodzinkio)methan mit zwei unterschiedlichen Elektrophilen^†

Corresponding Author

Prof. Kiitiro Utimoto

Department of Material Chemistry, Graduate School of Engineering Kyoto University Yoshida, Sakyo, Kyoto, 606–01 (Japan) Telefax: Int. + 75/753-4863 E-mail: [email protected]

Department of Material Chemistry, Graduate School of Engineering Kyoto University Yoshida, Sakyo, Kyoto, 606–01 (Japan) Telefax: Int. + 75/753-4863 E-mail: [email protected]Search for more papers by this author

Narihiro Toda,

Narihiro Toda

Department of Material Chemistry, Graduate School of Engineering Kyoto University Yoshida, Sakyo, Kyoto, 606–01 (Japan) Telefax: Int. + 75/753-4863 E-mail: [email protected]

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Takeshi Mizuno,

Takeshi Mizuno

Department of Material Chemistry, Graduate School of Engineering Kyoto University Yoshida, Sakyo, Kyoto, 606–01 (Japan) Telefax: Int. + 75/753-4863 E-mail: [email protected]

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Masami Kobata,

Masami Kobata

Department of Material Chemistry, Graduate School of Engineering Kyoto University Yoshida, Sakyo, Kyoto, 606–01 (Japan) Telefax: Int. + 75/753-4863 E-mail: [email protected]

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Dr. Seijiro Matsubara,

Dr. Seijiro Matsubara

Department of Material Chemistry, Graduate School of Engineering Kyoto University Yoshida, Sakyo, Kyoto, 606–01 (Japan) Telefax: Int. + 75/753-4863 E-mail: [email protected]

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Prof. Kiitiro Utimoto,

Corresponding Author

Prof. Kiitiro Utimoto

Department of Material Chemistry, Graduate School of Engineering Kyoto University Yoshida, Sakyo, Kyoto, 606–01 (Japan) Telefax: Int. + 75/753-4863 E-mail: [email protected]

Narihiro Toda,

Narihiro Toda

Department of Material Chemistry, Graduate School of Engineering Kyoto University Yoshida, Sakyo, Kyoto, 606–01 (Japan) Telefax: Int. + 75/753-4863 E-mail: [email protected]

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Takeshi Mizuno,

Takeshi Mizuno

Department of Material Chemistry, Graduate School of Engineering Kyoto University Yoshida, Sakyo, Kyoto, 606–01 (Japan) Telefax: Int. + 75/753-4863 E-mail: [email protected]

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Masami Kobata,

Masami Kobata

Department of Material Chemistry, Graduate School of Engineering Kyoto University Yoshida, Sakyo, Kyoto, 606–01 (Japan) Telefax: Int. + 75/753-4863 E-mail: [email protected]

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Dr. Seijiro Matsubara,

Dr. Seijiro Matsubara

Department of Material Chemistry, Graduate School of Engineering Kyoto University Yoshida, Sakyo, Kyoto, 606–01 (Japan) Telefax: Int. + 75/753-4863 E-mail: [email protected]

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First published: 15. Dezember 1997

https://doi.org/10.1002/ange.19971092418

Citations: 4

^†

Diese Arbeit wurde vom Ministerium für Erziehung, Wissenschaft, Sport und Kultur unterstützt (Grant in Aid Nr. 06403025, 09231223, 09238221).

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Abstract

[Pd₂(dba)₃] katalysiert in Gegenwart von Trifurylphosphan (TFP) die sukzessive Umsetzung von CH₂(ZnI)₂ mit verschiedenen Elektrophilen [G1. (a)]. Die homologe Zn₂-Verbindung CH₃CH(ZnI)₂ reagiert im 1. Schritt analog mit Cinnamylchlorid; für die Kupplung mit Allylbromid im zweiten Schritt ist aber CuCN/LiCN in stöchiometrischen Mengen nötig. CH₂(ZnI)₂+RXRCH₂ERXPhCHCHCH₂Cl, n-C₈H₁₇CCCH₂Br, C₂H₅CCCH(n-C₅H₁₁)Br EXDCl/D₂O, CH₂CHCH₂Br, PhCOCl. (a)

References

1 I. Marek, J.-F. Normant, Chem. Rev. 1996, 96, 3241–3267;
10.1021/cr9600161
CAS PubMed Web of Science® Google Scholar
F. Bickelhaupt, Angew. Chem. 1987, 99, 1020–1035;
10.1002/ange.19870991007
CAS Web of Science® Google Scholar
Angew. Chem. Int. Ed. Engl. 1987, 26, 990–1005;
10.1002/anie.198709901
Web of Science® Google Scholar
P. Knochel, J. F. Normant, Tetrahedron Lett. 1986, 27, 5727.
10.1016/S0040-4039(00)85311-3
CAS Web of Science® Google Scholar
2 R. J. J. Van de Heisteeg, G. Schat, M. A. G. M. Tinga, O. S. Akkerman, F. Bickelhaupt, Tetrahedron Lett. 1986, 27, 6123–6126;
10.1016/S0040-4039(00)85414-3
CAS Web of Science® Google Scholar
M. Hogenbirk, N. J. Van Eikema Hommes, G. Schat, O. S. Akkerman, F. Bickelhaupt, Tetrahedron Lett. 1989, 30, 6195–6198.
10.1016/S0040-4039(01)93340-4
CAS Web of Science® Google Scholar
3a) Cr: K. Takai, K. Nitta, K. Utimoto, J. Am. Chem. Soc. 1986, 108, 7408;
10.1021/ja00283a046
CAS Web of Science® Google Scholar
T. Okazoe, K. Takai, K. Utimoto, J. Am. Chem. Soc. 1987, 109, 951;
10.1021/ja00237a081
CAS Web of Science® Google Scholar
D. M. Hodgson, J. Organomet. Chem. 1994, 476, 1;
10.1016/0022-328X(94)84132-2
CAS Web of Science® Google Scholar
b) Cr-Sm: S. Matsubara, M. Horiuchi, K. Takai, K. Utimoto, Chem. Lett. 1995, 259–260;
Google Scholar
c) Zn-TiCl₄: T. Okazoe, K. Takai, K. Oshima, K. Utimoto, J. Org. Soc. 1987, 52, 4410;
10.1021/jo00228a055
CAS Web of Science® Google Scholar
K. Takai, Y. Kataoka, T. Okazoe, K. Utimoto, Tetrahedron Lett. 1988, 29, 1065–1068;
10.1016/0040-4039(88)85336-X
CAS Web of Science® Google Scholar
K. Takai, Y. Kataoka, J. Miyai, T. Okazoe, K. Oshima, K. Utimoto, Org. Synth. 1996, 73, 73–84;
10.15227/orgsyn.073.0073
CAS Web of Science® Google Scholar
L. Lombardo, Org. Synth. 1987, 65, 81–89.
10.15227/orgsyn.065.0081
CAS Google Scholar
4 P. Knochel, J. F. Normant, Tetrahedron Lett. 1986, 27, 4427–4430, 4431–4434;
10.1016/S0040-4039(00)84969-2
CAS Web of Science® Google Scholar
F. Chemla, I. Marek, J. F. Normant, Synlett 1993, 665–668;
Google Scholar
E. Nakamura, K. Kubota, G. Sakata, J. Am. Chem. Soc. 1997, 119, 5457–5458.
10.1021/ja9706357
CAS Web of Science® Google Scholar
5a) K. Takai, T. Kakiuchi, Y. Kataoka, K. Utimoto, J. Org. Chem. 1994, 59, 2668–2670;
10.1021/jo00089a002
CAS Web of Science® Google Scholar
b) K. Utimoto, T. Mizuno, M. Kobata, S. Matsubara, K. Takai, unveröffentlicht.
Google Scholar
6 Übersicht über die Reaktion von Organozinkverbindungen unter Pd-Katalyse: P. Knochel, R. D. Singer, Chem. Rev. 1993, 93, 2117–2188;
10.1021/cr00022a008
CAS Web of Science® Google Scholar
P. Knochel, Synlett 1995, 393–403.
Google Scholar
7 Der im ersten Schritt verwendete Palladium-Katalysator ist immer noch aktiv und katalysiert auch die zweite Teilreaktion.
Google Scholar
8 Übersicht zu Kupfer-vermittelten Reaktionen von Organozinkverbindungen mit Elektrophilen: Lit. [6].
Google Scholar

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Volume109, Issue24

15. Dezember 1997

Pages 2886-2888

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Sukzessive Reaktion von Bis(iodzinkio)methan mit zwei unterschiedlichen Elektrophilen^†

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Sukzessive Reaktion von Bis(iodzinkio)methan mit zwei unterschiedlichen Elektrophilen†

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Sukzessive Reaktion von Bis(iodzinkio)methan mit zwei unterschiedlichen Elektrophilen^†