Preparation and Reactions of Functionalized Benzylic Organometallics of Zinc And Copper

Scott C. Berk, Ming Chang P. Yen, Nakcheol Jeong, Paul Knochel

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Abstract

The reaction of zinc dust with primary or secondary benzylic halides 1 bearing various functional groups such as an ester, halide, cyano, or even a ketone group, in THF or, in the case of benzylic chlorides, in THF:DMSO (4:1), furnishes the corresponding zinc organometallics 2 in high yields. The reaction is accompanied by less than 10% of Wurtz coupling products. The benzylic copper organometallics 3, obtained after a transmetalation of 2 with the THF-soluble copper salt CuCN·2LiCl at -20 °C, react in excellent yields (70-95%) with various electrophiles such as acid chlorides, enones, aldehydes, allylic bromides, ethyl propiolate, and tributyltin chloride, leading to the polyfunctional molecules of type 4.

Original languageEnglish
Pages (from-to)3053-3064
Number of pages12
JournalOrganometallics
Volume9
Issue number12
DOIs
Publication statusPublished - 1990 Jan 1

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ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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