Abstract
The Suzuki–Miyaura coupling reaction is one of the most widely utilized C–C bond forming methods to create (hetero)biaryl scaffolds. The continuous-flow reaction using heterogeneous catalyst-packed cartridges is a practical and efficient synthetic method to replace batch-type reactions. A continuous-flow ligand-free Suzuki–Miyaura coupling reaction of (hetero)aryl iodides, bromides, and chlorides with (hetero)aryl boronic acids was developed using cartridges packed with spherical resin (tertiary amine-based chelate resin: WA30)-supported palladium catalysts (7% Pd/WA30). The void space in the cartridge caused by the spherical catalyst structures enables the smooth flow of a homogeneously dissolved reaction solution that consists of a mixture of organic and aqueous solvents and is delivered by the use of a single syringe pump. Clogging or serious backpressure was not observed.
Highlights
The Suzuki–Miyaura reaction [1,2,3,4,5,6,7] is robust and is one of the most reliable C–C bond-forming methods
The continuous-flow Suzuki–Miyaura coupling reaction ofaromatic iodides, bromides, and chlorides witharyl boronic acids was developed using 7% Pd/WA30-packed catalyst cartridges, where Pd was immobilized on the spherical chelate resin WA30
Coupling of aromatic iodides and bromides with aryl boronic acids was efficiently conducted by transferring a single reaction solution of aryl halides, aryl boronic acids, and inorganic bases dissolved in H2 O/1,4-dioxane into a 7% Pd/WA30-packed catalyst cartridge using a syringe pump
Summary
The Suzuki–Miyaura reaction [1,2,3,4,5,6,7] is robust and is one of the most reliable C–C bond-forming methods. It is utilized for the production of (hetero)biaryl structures, which are fundamental components of active pharmaceutical ingredients (APIs) [4,8,9,10,11,12,13,14], functional materials [15], and natural products [16,17] in a variety of synthetic chemistry fields. Supported Pd catalysts packed in a cartridge can be safely utilized without deactivation or ignition because the catalyst is not exposed to air (especially atmospheric oxygen)
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