Development of a fluorous, oxime-based palladacycle for microwave-promoted carbon–carbon coupling reactions in aqueous media

Extraction of Base from Eichhornia crassipes and Its Implication in Palladium‐Catalyzed Suzuki Cross‐Coupling Reaction

“…Usually, catalytic systems for these transformations are composed of Pd(0) or Pd(II) derivatives. Recently, different ligands such as N‐heterocyclic carbenes, amines, oximes,, amides, and their co‐ordination with palladium have attracted considerable attention as catalyst for Suzuki‐Miyaura Cross‐Coupling reaction. However, in most of the cases, main disadvantages associated are the availability, stability and cost of the Pd complexes and associated ligands and their moisture sensitivity.…”

Fluorous Organometallic Chemistry

“…In 2011, a series of luminescent iridium(III) biscyclometalated cations [Ir(N-C) 2 (N-N)](PF 6 ) with two C 8 F 17 ponytails were reported, in which the fluorous substituents appeared to impact positively on the photophysical and biological properties [121]. The oxime-based palladacycle (24), formed in a slow reaction of the free oxime with Li 2 PdCl 4 in acetone at reflux, has been shown to be a highly effective pre-catalyst for SuzukiMiyaura, Sonagashira, Stille, Heck and Kumada reactions, either in aqueous solution or organic solvents, that could be recycled and reused up to five times [122,123]. The first metal-pincer ligand complex was reported in 1998.…”

Eco-Friendly Physical Activation Methods for Suzuki–Miyaura Reactions

“…This product can be subsequently submitted to SMC with phenylboronic acid under aqueous conditions to obtain the desired diarylated derivative (Scheme 31). Susanto et al [66] have developed a fluorous, thermally stable oxime-derived palladacycle for MW-enhanced carbon-carbon SMC reactions in aqueous media. The palladacycle gave extremely low levels of Pd leaching (0.023-0.033 ppm over 5 cycles) and was reused five times with no significant loss in activity.…”

“…A benzothiazole-oxime Pd(II)-complex was successfully applied for this proposal either in water or DMF enabling good SMC product yields in 10-30 min under MW irradiation at 100-160 °C (Scheme 33). Susanto et al [66] have developed a fluorous, thermally stable oxime-derived palladacycle for MW-enhanced carbon-carbon SMC reactions in aqueous media. The palladacycle gave extremely low levels of Pd leaching (0.023-0.033 ppm over 5 cycles) and was reused five times with no significant loss in activity.…”