• Home
  • Search Results
  • Palladium-catalyzed alkenylation of quinoline-N-oxides via C-H activation under external-oxidant-free conditions.

Palladium-catalyzed alkenylation of quinoline-N-oxides via C-H activation under external-oxidant-free conditions.

Journal of the American Chemical Society (2009-09-15)
Junliang Wu, Xiuling Cui, Lianmei Chen, Guojie Jiang, Yangjie Wu
ABSTRACT

The direct cross-coupling of quinoline-N-oxides with olefin derivatives has been realized using palladium acetate as the catalyst in the absence of external ligand and oxidant to give the corresponding 2-alkenylated quinolines and 1-alkenylated isoquinolines chemo- and regioselectively in 27-95% yield. The catalytic process is proposed to proceed via direct C-H bond activation of the quinoline-N-oxide with Pd(OAc)(2) followed by Heck coupling with the olefin. The resultant N-oxide of the alkenylated quinoline can oxidize the reduced Pd(0) to regenerate the Pd(II) active species and simultaneously release the 2-alkenylated quinoline without using any external oxidants and reductants.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ethyl acrylate, contains 10-20 ppm MEHQ as inhibitor, 99%
Supelco
Ethyl acrylate, analytical standard
Sigma-Aldrich
Ethyl acrylate, ≥99.5%, stabilized

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.