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Pseudo‐Solid‐State Suzuki–Miyaura Reaction and the Role of Water Formed by Dehydration of Arylboronic Acids
Author(s) -
Pentsak Evgeniy O.,
Ananikov Valentine P.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900410
Subject(s) - chemistry , sublimation (psychology) , catalysis , coupling reaction , halide , solvent , aryl , organic chemistry , leaching (pedology) , aryl halide , polymer chemistry , palladium , psychology , alkyl , environmental science , soil science , psychotherapist , soil water
Solvent‐free reactions belong to a very attractive area of organic chemistry. The solvent‐free Suzuki–Miyaura coupling is of special importance due to the problem of catalyst leaching in the presence of a solvent. This study investigates the course of reaction of solid aryl halides with arylboronic acids in the absence of a solvent and without any liquid additives. For the first time, a number of important conditions for performing a solid‐state Suzuki–Miyaura reaction were analyzed in details. The results indicate a prominent role of water, which is formed as a by‐product in the side reaction of arylboronic acid trimerization. Electron microscopy study revealed surprising changes occurring within the reaction mixture during the reaction and indicated the formation of spherical nano‐sized particles containing the reaction product. Catalyst recycling was easily performed in the developed system and the product was isolated by sublimation, thus providing a possibility to completely avoid the use of solvents at all stages.