Cobalt‐Catalyzed Cross‐Couplings between Alkenyl Acetates and Aryl or Alkenyl Zinc Pivalates

Abstract

CoBr (5 mol %) in the presence of 2,2'-bipyridyl (5 mol %) enables electrophilic alkenylations between easily accessible alkenyl acetates or tosylates and various functionalized aryl zinc pivalates at ambient temperature. This cobalt-catalyzed process was further applicable to alkenyl zinc pivalates to provide substituted 1,3-dienes.

Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines

“…We have extended this preparation of quinoline derivatives by treating various anthranils ( 2 ) with alkenylzinc pivalates 13 under our standard conditions. To our delight, we observed after the electrophilic amination step, an cycloisomerisation which in a one-pot procedure provided the quinolines 8a – 8n in 62–96% yields (Scheme 3).…”

Palladium‐Catalyzed Cross‐Coupling of Alkenyl Carboxylates

“…Unfortunately, using alkenyl acetates in cross‐coupling remains challenging. The most general catalysts currently reported require sensitive organometallic nucleophiles or bases (Scheme a) . While powerful, these methods can be procedurally complex, especially for generating highly‐functionalized substrates.…”

Société Chimique de France Prizes 2018: J. A. Baceiredo, P. Samorì, P. Knochel, Z. Shuai, F. Lloret Pastor, A. J. L. Pombeiro / Sir William Grove Award: P. Strasser / Jaroslav Heyrovsky Prize: S. Waldvogel

“…Knochel and his group are interested in the development of new organometallic catalysts and reagents for organic synthesis, as well as the preparation of polyfunctional organometallics, asymmetric synthesis, and natural product synthesis. He has reported in Chemistry—A European Journal on the synthesis of polyfunctionalized triaryllanthanum reagents, and in Angewandte Chemie on cobalt‐catalyzed cross‐coupling reactions . Knochel is on the Editorial Board of ChemPlusChem and the International Advisory Board of Chemistry—An Asian Journal .…”