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Suzuki Coupling in Flow Reactors

Mechanism + Description

As for Suzuki reaction with soluble catalysts

General comments

The Suzuki reaction chemistry is amenable to operation in flow as well as batch processing, and in some cases may benefit from continuous processing. The reaction also seems to be accelerated by microwave heating, often used in conjunction with flow reactors. The catalyst can be homogeneous or heterogeneous.

Key references

Park, J. H.; Park, C. Y.; Kim, M. J.; Kim, M. U.; Kim, Y. J.; Kim; G.; Park, C. P. Continuous-Flow Synthesis of meta-Substituted Phenol Derivatives. Org. Process Res. Dev. 2015, 19 (7), 812–818.

Konda, V.; Rydfjord, J.; Sävmarker, J.; Larhed, M. Safe Palladium-Catalyzed Cross-Couplings with Microwave Heating Using Continuous-Flow Silicon Carbide Reactors. Org. Process Res. Dev. 2014, 18 (11), 1413–1418.

Gürsel, I. V.; Noël, T.; Wang, Q.; Hessel, V. Separation/Recycling Methods for Homogeneous Transition Metal Catalysts in Continuous Flow. Green Chem. 2015,17 (4), 2012-2026.

Noël, T.; Hessel, V. Cross-Coupling Chemistry in Continuous Flow. New Trends in Cross-Coupling: Theory and Applications; Catalysis Series; Royal Society of Chemistry: Cambridge, U.K., 2014; 610-644.

Leeke, G. A.; Santos, R. C. D.; Al-Duri, B.; Seville, J. P. K.; Smith, C. J.; Lee, C. K. Y.; Holmes, A. B.; McConvey, I. F. Continuous-Flow Suzuki−Miyaura Reaction in Supercritical Carbon Dioxide. Org. Process Res. Dev. 2007, 11 (1), 144–148.

Pandarus, V.; Gingras, G.; Béland, F.; Ciriminna, R.; Pagliaro, M. Process Intensification of the Suzuki−Miyaura Reaction over Sol−Gel Entrapped Catalyst SiliaCat DPP-Pd Under Conditions of Continuous Flow. Org. Process Res. Dev. 2014, 18 (11), 1550−1555.

Cantillo, D.; Kappe, C. O. Immobilized Transition Metals as Catalysts for Cross-Couplings in Continuous Flow—A Critical Assessment of the Reaction Mechanism and Metal Leaching. ChemCatChem . 2014, 6 (12), 3286-3305.

Mateos, C.; Rincón, J. A.; Martín-Hidalgo, B.; Villanueva, J. Green and Scalable Procedure for Extremely Fast LigandlessSuzuki–MiyauraCross-Coupling Reactions in Aqueous IPA Using Solid-Supported Pd in Continuous Flow. Tetrahedron Lett. 2014, 55 (27), 3701-3705.

Relevant Scale-Up Examples with Scheme

Org. Process Res. Dev. 2014, 18 (11), 1345−1353.
Multi g scale