A General and Special Catalyst for Suzuki–Miyaura Coupling Processes

Abstract

Biaryl monophosphorus ligands containing a 2,3‐dihydrobenzo[d][1,3]oxaphosphole framework are highly effective for the palladium‐catalyzed Suzuki–Miyaura cross‐coupling reactions of a wide range of substrates. Ligand 1 has demonstrated excellent performance for coupling reactions of extremely hindered arylboronic acids.

Oxaphosphole‐Based Monophosphorus Ligands for Palladium‐Catalyzed Amination Reactions

“…[18] The effectiveness of ligand 6 (BI-DIME) was demonstrated in palladium-catalyzed Suzuki-Miyaura coupling reactions of various aryl and heteroaryl bromides and chlorides with sterically congested and electron-poor arylboronic acids. The application of monophosphines 5-7 in amination reactions was also the subject of the present investigation.…”

Hydrolysis of 8-(pinacolboranyl)quinoline: where is the 8-quinolylboronic acid?

“…We note that '8-quinolylboronic acid' or derivatives have been utilized successfully in Suzuki coupling reactions [24,25,[27][28][29][30][31][32]. In the mechanism, boronate ions are typically invoked as solution intermediates that transfer an aryl group to Pd in a transmetalation step that ultimately leads to C-C bond formation upon reductive elimination from the Pd center.…”

Clustering of palladium(II) chloride in acetonitrile solution investigated by electrospray mass spectrometry

“…Particularly C-C coupling reactions catalyzed by palladium catalysts, such as the Heck, Sonogashira, Suzuki, or Stille reactions, are of high importance in organic synthesis [5][6][7]. The formation of appropriate precatalysts with suitable ligands (phosphines, N-heterocarbenes, etc.)…”