The development of efficient catalysts for palladium-catalyzed coupling reactions of aryl halides

Abstract

In the mid 1990s, we started a program on the development of more efficient palladium catalysts for the C-C and C-N coupling reactions of aryl halides, especially aryl chlorides. In this contribution, our investigations on new catalyst systems and their application in organic synthesis are summarized.

Heck Reaction—State of the Art

“…In a similar review by Zapf and Beller [26], ligands and palladacycles 51, 99 and 110 to 115 ( Figure 12) are reviewed for their activity towards the C-C and C-N coupling reactions of aryl halides, especially aryl chlorides. An important advantage of this class of ligands is their significantly increased stability towards air and moisture.…”

A General and Efficient Method for the Formylation of Aryl and Heteroaryl Bromides

“…[11] For some time we have been involved in the development of new ligands and catalysts for coupling reactions of aryl halides. [12,13] Recent examples include diadamantylalkylphosphines, [14,15] and N-aryl-substituted heteroaryldialkylphosphines, [16] which lead to highly active catalysts, but are comparably stable to air and moisture, and thus easy to handle.…”

Novel tetrahydropyrimidinium / palladium system as a convenient catalyst: Suzuki coupling reactions of aryl chlorides

“…Many different catalytic applications of NHC complexes have been described. [15][16][17] Palladium-catalysed cross-coupling reactions are particularly attractive because of their versatility for formation of C-C bonds. [18][19][20] Sterically hindered, electron-rich alkyl phosphines 21 and carbene 22 ligands have received growing interest in recent years.…”