A Palladium NNC‐Pincer Complex as an Efficient Catalyst Precursor for the Mizoroki−Heck Reaction

Abstract

The Mizoroki−Heck reaction of aryl halides (iodides, bromides, or chlorides) with activated alkenes in the presence of a palladium NNC‐pincer complex at ppb to ppm loadings gave the corresponding internal alkenes in excellent yields. The total turnover number and turnover frequency reached up to 8.70×108 and 1.21×107 h−1 (3.36×103 s−1), respectively. The catalyst was applied in a ten‐gram‐scale synthesis of the UV‐B sunscreen agent octinoxate (2‐ethylhexyl 4‐methoxycinnamate). Reaction‐rate analyses, transmission electron microscopic examination of the reaction mixture, and poisoning tests suggested that a monomeric palladium species is the catalytically active species in the catalytic cycle.magnified image

Magnetite tethered mesoionic carbene‐palladium (II): An efficient and reusable nanomagnetic catalyst for Suzuki‐Miyaura and Mizoroki‐Heck cross‐coupling reactions in aqueous medium

“…Also, MNPs‐MIC‐Pd nanomagnetic catalyst is superior in terms of non‐toxicity, price, stability and ease of separation than the previously reported ones. Furthermore, the recyclability MNPs‐MIC‐Pd nanomagnetic catalyst is easier and rapid than those of other reported catalysts …”

“…Furthermore, the recyclability MNPs-MIC-Pd nanomagnetic catalyst is easier and rapid than those of other reported catalysts. [38][39][40][41]43,[47][48][49][50][51][52][53][54][55][56][57][58][59][60]…”

Palladium‐Based Catalysts Supported by Unsymmetrical XYC–1 Type Pincer Ligands: C5 Arylation of Imidazoles and Synthesis of Octinoxate Utilizing the Mizoroki–Heck Reaction

“…Unsymmetrical pincer palladacycles are comparatively novel, however, the synthesis of their respective ligands often possess difficulty than their symmetrical ligands. [9d]…”

Oxime‐derived palladacycle Immobilized in an Ionic Liquid Brush as an Efficient and Reusable Catalyst for Mozoroki‐Heck Reaction in Neat Water

“…Some heterogeneous catalysts have been applied to Mizoroki–Heck reaction, in order to overcome the incompatibility of lipophilic substrates and inorganic base, many of them were carried out in toxic organic solvent such as DMF, DMA,, MeCN and NMP, which can bring about environmental pollution. Driven by economic and environmental concerns, the use of a clean and environmentally friendly reaction medium to replace the traditional organic solvent is an important research topic to realize a green Mizoroki–Heck reaction.…”