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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)570-577
Number of pages8
JournalJournal of Organic Chemistry
Volume66
Issue number2
DOIs
Publication statusPublished - Jan 26 2001

    Fingerprint

ASJC Scopus subject areas

  • Organic Chemistry

Cite this