Selective activation of carbon-carbon bonds next to a carbonyl group
Abstract
ORGANOMETALLIC complexes are used to effect a wide range of catalytic transformations in organic synthesis, such as the activation of C-H bonds1,2. Carbon-carbon bonds, however, are generally unreactive towards transition metals under homogeneous conditions. C-C bond activation by a process of oxidative addition to soluble transition-metal complexes has been limited mostly to stoichiometric (not catalytic) reactions1,3-7,18, to highly strained substrates such as cyclopropane and cubane1,8-11 or to chelating ketones19. Here we present a synthetically useful process of selective C-C bond activation in which the C-C bond adjacent to a carbonyl group is opened by insertion of a soluble rhodium(I) complex. The resulting organometallic intermediate can be transformed to a variety of products in a way that regenerates the rhodium complex. We anticipate that this catalytic scheme will have considerable utility in organic synthesis.
- Publication:
-
Nature
- Pub Date:
- August 1994
- DOI:
- 10.1038/370540a0
- Bibcode:
- 1994Natur.370..540M