Synthesis and utilization of organocopper(I) ate complexes from Grignard reagents Academic Article uri icon

abstract

  • Organocopper(I) ate complexes can be prepared in high yield from methylcopper(I) and aliphatic or aryl Grignard reagents. The resulting complexes efficiently transfer the Grignard reagent derived primary, secondary, tertiary, or aryl group in reactions in acyl chlorides leading to ketones. This synthetic method is illustrated with procedures for CH3(CH2)15COCH3, C6H5COC6H5, CH3(CH2)2CH(CH3)COCH3, (CH3)3CCOC6H5, p-CH3C6H4COC6H5, C6H6COCH3, (CH3)3CCOC(CH3)3, and C6H5CO(CH2)CH3. This reaction provides a general and useful alternative to syntheses of organocopper(I) ate complexes from organolithium reagents. Methylcopper(I) is shown to be significantly better than other copper(I) species for forming reactive organocopper(I) ate complexes from Grignard reagents. © 1976, American Chemical Society. All rights reserved.

author list (cited authors)

  • Bergbreiter, D. E., & Killough, J. M.

citation count

  • 47

publication date

  • August 1976