Sterically enhanced 2‐iminopyridylpalladium chlorides as recyclable ppm‐palladium catalyst for Suzuki–Miyaura coupling in aqueous solution
- 19 October 2021
- journal article
- research article
- Published by Wiley in Applied Organometallic Chemistry
- Vol. 36 (1) , e6474
Abstract
Sterically hindered 2‐iminopyridine derivatives and their palladium chlorides complexes are designed and prepared, which efficiently promote the Suzuki–Miyaura coupling (SMC) reaction in aqueous solution. Besides the good to excellent yields and broad substrate scope, these catalysts can be reused for at least four new batches of the substrates. Spontaneous separation of coupling products in the aqueous reaction medium is the additional striking feature of this catalytic process. Furthermore, catalytic performance of palladium complexes bearing the azo‐bridged phenyl groups was greatly influenced by the UV irradiation due to the cis/trans photoisomerization of azo unit of the catalysts. In conclusion, titled palladium complexes provide a green, sustainable, cost‐effective, and convenient process to synthesize SMC products at multi‐gram‐scale reaction.Keywords
Funding Information
- National Natural Science Foundation of China (21871275, 21801098)
This publication has 61 references indexed in Scilit:
- Palladium‐Catalyzed Cross‐Coupling: A Historical Contextual Perspective to the 2010 Nobel PrizeAngewandte Chemie International Edition, 2012
- Nanocatalysts for Suzuki cross-coupling reactionsChemical Society Reviews, 2011
- Catalysis by Palladium Pincer ComplexesChemical Reviews, 2010
- Effects of Different Terminal Substituents on the Mesomorphic Behavior of Some Azo-Schiff Base and Azo-Ester-Based Liquid CrystalsMolecular Crystals and Liquid Crystals, 2010
- Recent Applications of Palladium‐Catalyzed Coupling Reactions in the Pharmaceutical, Agrochemical, and Fine Chemical IndustriesAdvanced Synthesis & Catalysis, 2009
- OLEX2: a complete structure solution, refinement and analysis programJournal of Applied Crystallography, 2009
- Recycling of homogeneous Pd catalysts using superparamagnetic nanoparticles as novel soluble supports for Suzuki, Heck, and Sonogashira cross-coupling reactionsChemical Communications, 2005
- A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halidesTetrahedron Letters, 1979
- Stereoselective synthesis of arylated (E)-alkenes by the reaction of alk-1-enylboranes with aryl halides in the presence of palladium catalystJournal of the Chemical Society, Chemical Communications, 1979
- Emulsion stabilization by non-ionic surfactants: the relevance of surfactant cloud pointJournal of Pharmacy and Pharmacology, 1975