Distannane mediated reaction of N-acyliminium ion pools with alkyl halides. A chain mechanism involving radical addition followed by electron transfer

Tomokazu Maruyama; Seiji Suga; Jun ichi Yoshida

doi:10.1016/j.tet.2006.03.114

Distannane mediated reaction of N-acyliminium ion pools with alkyl halides. A chain mechanism involving radical addition followed by electron transfer

Tomokazu Maruyama, Seiji Suga, Jun ichi Yoshida

Research output: Contribution to journal › Article › peer-review

33 Citations (Scopus)

Abstract

Hexabutyldistannane was found to be an effective mediator allowing the reaction of N-acyliminium ion pools with alkyl halides. A chain mechanism involving the addition of an alkyl radical generated from an alkyl halide to an N-acyliminium ion followed by the one-electron reduction of the resulting radical-cation by distannane was proposed.

Original language	English
Pages (from-to)	6519-6525
Number of pages	7
Journal	Tetrahedron
Volume	62
Issue number	27
DOIs	https://doi.org/10.1016/j.tet.2006.03.114
Publication status	Published - Jul 3 2006
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2006.03.114

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title = "Distannane mediated reaction of N-acyliminium ion pools with alkyl halides. A chain mechanism involving radical addition followed by electron transfer",

abstract = "Hexabutyldistannane was found to be an effective mediator allowing the reaction of N-acyliminium ion pools with alkyl halides. A chain mechanism involving the addition of an alkyl radical generated from an alkyl halide to an N-acyliminium ion followed by the one-electron reduction of the resulting radical-cation by distannane was proposed.",

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AU - Maruyama, Tomokazu

AU - Suga, Seiji

AU - Yoshida, Jun ichi

PY - 2006/7/3

Y1 - 2006/7/3

N2 - Hexabutyldistannane was found to be an effective mediator allowing the reaction of N-acyliminium ion pools with alkyl halides. A chain mechanism involving the addition of an alkyl radical generated from an alkyl halide to an N-acyliminium ion followed by the one-electron reduction of the resulting radical-cation by distannane was proposed.

AB - Hexabutyldistannane was found to be an effective mediator allowing the reaction of N-acyliminium ion pools with alkyl halides. A chain mechanism involving the addition of an alkyl radical generated from an alkyl halide to an N-acyliminium ion followed by the one-electron reduction of the resulting radical-cation by distannane was proposed.

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Distannane mediated reaction of N-acyliminium ion pools with alkyl halides. A chain mechanism involving radical addition followed by electron transfer

Abstract

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