Reductive cross-coupling of 3-substituted Δ3-cephems with alkenyl halides in an Al/PbBr2/NiBr2(bpy) triplemetal redox system. Synthesis of 3-alkenyl-Δ3-cephems

H. Tanaka; J. Zhao; H. Kumase

doi:10.1021/jo001429b

Reductive cross-coupling of 3-substituted Δ³-cephems with alkenyl halides in an Al/PbBr₂/NiBr₂(bpy) triplemetal redox system. Synthesis of 3-alkenyl-Δ³-cephems

H. Tanaka, J. Zhao, H. Kumase

Faculty of Engineering

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

7 Citations (Scopus)

Abstract

Synthesis of 3-alkenyl-Δ³-cephems was performed successfully by cross-coupling 3-(trifluoromethylsulfonyloxy or chloro)-Δ³-cephem with alkenyl halides, e.g., vihyl bromide, trans-1-bromo-1-propene, and trans-β-bromostyrene in an Al/cat·PbBr₂/cat·NiBr₂(bpy)/NMP (or DMF) system. Reduction of 3-(trifluoromethylsulfonyloxy)-Δ³-cephem into norcephalosporin was also achieved by a similar reaction in the presence of 5 molar equiv of water. Scope and a plausible mechanism of the Al/Pb/Ni triplemetal-redox promoted reactions are discussed.

Original language	English
Pages (from-to)	570-577
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	66
Issue number	2
DOIs	https://doi.org/10.1021/jo001429b
Publication status	Published - Jan 26 2001

ASJC Scopus subject areas

Organic Chemistry

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title = "Reductive cross-coupling of 3-substituted Δ3-cephems with alkenyl halides in an Al/PbBr2/NiBr2(bpy) triplemetal redox system. Synthesis of 3-alkenyl-Δ3-cephems",

abstract = "Synthesis of 3-alkenyl-Δ3-cephems was performed successfully by cross-coupling 3-(trifluoromethylsulfonyloxy or chloro)-Δ3-cephem with alkenyl halides, e.g., vihyl bromide, trans-1-bromo-1-propene, and trans-β-bromostyrene in an Al/cat·PbBr2/cat·NiBr2(bpy)/NMP (or DMF) system. Reduction of 3-(trifluoromethylsulfonyloxy)-Δ3-cephem into norcephalosporin was also achieved by a similar reaction in the presence of 5 molar equiv of water. Scope and a plausible mechanism of the Al/Pb/Ni triplemetal-redox promoted reactions are discussed.",

author = "H. Tanaka and J. Zhao and H. Kumase",

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doi = "10.1021/jo001429b",

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T1 - Reductive cross-coupling of 3-substituted Δ3-cephems with alkenyl halides in an Al/PbBr2/NiBr2(bpy) triplemetal redox system. Synthesis of 3-alkenyl-Δ3-cephems

AU - Tanaka, H.

AU - Zhao, J.

AU - Kumase, H.

PY - 2001/1/26

Y1 - 2001/1/26

N2 - Synthesis of 3-alkenyl-Δ3-cephems was performed successfully by cross-coupling 3-(trifluoromethylsulfonyloxy or chloro)-Δ3-cephem with alkenyl halides, e.g., vihyl bromide, trans-1-bromo-1-propene, and trans-β-bromostyrene in an Al/cat·PbBr2/cat·NiBr2(bpy)/NMP (or DMF) system. Reduction of 3-(trifluoromethylsulfonyloxy)-Δ3-cephem into norcephalosporin was also achieved by a similar reaction in the presence of 5 molar equiv of water. Scope and a plausible mechanism of the Al/Pb/Ni triplemetal-redox promoted reactions are discussed.

AB - Synthesis of 3-alkenyl-Δ3-cephems was performed successfully by cross-coupling 3-(trifluoromethylsulfonyloxy or chloro)-Δ3-cephem with alkenyl halides, e.g., vihyl bromide, trans-1-bromo-1-propene, and trans-β-bromostyrene in an Al/cat·PbBr2/cat·NiBr2(bpy)/NMP (or DMF) system. Reduction of 3-(trifluoromethylsulfonyloxy)-Δ3-cephem into norcephalosporin was also achieved by a similar reaction in the presence of 5 molar equiv of water. Scope and a plausible mechanism of the Al/Pb/Ni triplemetal-redox promoted reactions are discussed.

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Reductive cross-coupling of 3-substituted Δ³-cephems with alkenyl halides in an Al/PbBr₂/NiBr₂(bpy) triplemetal redox system. Synthesis of 3-alkenyl-Δ³-cephems

Abstract

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