1. Functionalizing heterocycles by electron-deficient bonding to a triosmium cluster
- Author
-
Bergman, Brian, Holmquist, Richard, Smith, Ryan, Rosenberg, Edward, Ciurash, Joana, Hardcastle, Kenneth, and Visi, Mandana
- Subjects
Organic compounds -- Synthesis ,Quinoline -- Research ,Heterocyclic compounds -- Research ,Chemistry - Abstract
A novel synthetic approach for the addition of carbon-based nucleophiles to the carbocyclic ring of quinolines is presented. The C(5) carbon of the quinoline ring is vulnerable to regiospecific attack by a broad range of carbanions, as the three-center, two-electron bonding of the C(8) carbon of the quinoline ring with two metal atoms of the Os3 triangle conveys a considerable electron deficiency to it. The development of the new synthetic methodology was prompted by the recent synthesis of a family of quinoline compounds that undergo regioselective nucleophilic addition of hydride at the 5-position.
- Published
- 1998