Cyclopalladated ferrocenylimines: highly active catalysts for Heck reactions

High‐Turnover Palladium Catalysts in Cross‐Coupling and Heck Chemistry: A Critical Overview

“…Imine-and oxime-derived palladacycles have been introduced as the most effective phosphane-free catalytic systems in Heck and cross-coupling chemistry. For example, ferrocenylimine palladacycles 3a, b have shown TONs approaching 10 7 for simple Heck reactions, [83,84] and they have been shown to work well even in water, provided TBAB is added (PhI with ethyl acrylate at 80 8C, 2.8 Â 10 5 TON). [85] Milstein et al have reported somewhat lower TONs for the Heck reaction (10 5 - 10 6 ) using imine-palladacycle precatalyst 9b.…”

Synthesis, characterization and crystal structures of two cis/trans pyridine-cyclopalladated ferrocenylimine complexes

“…Among them, cyclopalladated ferrocene derivatives are particularly interesting since planar chirality may be introduced in the 1,2-disubstituted ferrocene moiety which shows great potential in asymmetric synthesis and catalysis [5,6]. In this respect, we have reported a variety of achiral and chiral cyclopalladated complexes having Schiff base type of ferrocenylimine ligands [7][8][9][10][11] and found that some cyclopalladated complexes are efficient catalysts for the Heck [9] and Suzuki reactions [10,11].…”

Chiral Platinum(II) Compounds Containing Ferrocenyl Schiff Bases Acting as (N), (N,O)–, [C(sp2,ferrocene),N]– or [C(sp2,ferrocene),N,O]2– Ligands

“…On the other hand, palladium(II) complexes containing (N), (N,E), (C,N) -or (C,N,E) -(E = NЈ, S or P) ferrocenyl ligands have attracted great interest in recent years, [12][13][14][15][16][17] mainly because of their applications in homogeneous catalysis [16] or in organometallic synthesis. [17] Platinum(II) analogues are less common [18,19] but some of these also exhibit antitumoral activity against cisplatin-resistant cells.…”