Convenient and Efficient Suzuki−Miyaura Cross-Coupling Catalyzed by a Palladium/Diazabutadiene System

Abstract

[structure: see text]. A Pd(OAc)2/diazabutadiene system has been developed for the catalytic cross-coupling of aryl halides with arylboronic acids. A combination of the diazabutadiene DAB-Cy (1, N,N'-dicyclohexyl-1,4-dizabutadiene) and Pd(OAc)2 was found to form an excellent catalyst for the Suzuki-Miyaura cross-coupling of various aryl bromides and activated aryl chlorides with arylboronic acids.

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

“…Nolan and co-workers 87 have developed a Pd(OAc) 2 /diazabutadiene system which mediates the catalytic cross-coupling reaction of aryl halides with arylboronic acids (Scheme 36). A combination of the diazabutadiene (N,N 0 -dicyclohexyl-1,4-diazabutadiene) and Pd(OAc) 2 was found to be an efficient catalyst for the SM cross-coupling reaction of various aryl bromides or activated aryl chlorides with arylboronic acids.…”

Density Functional Studies on Palladium‐Catalyzed Suzuki–Miyaura Cross‐Coupling Reactions Assisted by N‐ or P‐Chelating Ligands

“…More recently, Nolan and co-workers pioneered the use of a well-known family of N,N-bidentate ligands, the diazabutadienes, in the Suzuki-Miyaura cross-coupling reaction. [19] Ligands containing the 1,4-diaza-1,3-butadiene skeleton, R-di-A C H T U N G T R E N N U N G imines (DAB-R), are shown in Scheme 2. The chelating nature of these ligands also enhances the stability of the complexed metal compound.…”

Stereocontrolled Synthesis of (E)‐β,γ‐Unsaturated Esters via Palladium‐Catalyzed Cross‐Coupling of (E)‐Alkenylboronic Acids with α ‐Bromoacetic Esters

“…The addition of catalytic amount of Cu 2 O 16 did not improve the outcome (Entry 2). Using a catalytic system developed by Nolan et al,18 the yield of the cross-coupling product was also very low (Entry 3). The use of an electron-rich ligand D, tris(2-methylphenyl) phospine, increased the yield only to 36% (Entry 4).…”