The application of organic bases in microwave-promoted Suzuki coupling reactions in water

Traditionally, mineral bases are used in Suzuki coupling protocols. The use of DBU or DABCO as alternative bases for the reaction is reported and the application discussed.

[1]  Noel S. Wilson,et al.  Development and Applications of a Practical Continuous Flow Microwave Cell , 2004 .

[2]  W. Dehaen,et al.  Generation of a Small Library of Highly Electron‐Rich 2‐(Hetero)Aryl‐Substituted Phenethylamines by the Suzuki−Miyaura Reaction: A Short Synthesis of an Apogalanthamine Analogue , 2004 .

[3]  P. J. Persichini.  Carbon-Carbon Bond Formation via Boron Mediated Transfer , 2003 .

[4]  Andreas Kirschning,et al.  Continuous flow techniques in organic synthesis. , 2003, Chemistry.

[5]  N. A. Bumagin,et al.  Pd-EDTA as an efficient catalyst for suzuki-miyaura reactions in water , 2005 .

[6]  N. Leadbeater,et al.  A reassessment of the transition-metal free suzuki-type coupling methodology. , 2005, The Journal of organic chemistry.

[7]  C. Kappe,et al.  Microwave-enhanced reactions under open and closed vessel conditions. A case study , 2002 .

[8]  Paul Watts,et al.  Benchmarking of Microreactor Applications , 2004 .

[9]  W. König,et al.  Microwave-Assisted Aqueous Suzuki Cross-Coupling Reactions , 1999 .

[10]  K. Burgess,et al.  Microwave-assisted functionalization of bromo-fluorescein and bromorhodamine derivatives , 2003 .

[11]  A. Loupy.  Microwaves in organic synthesis , 2002 .

[12]  N. Leadbeater,et al.  Ligand-free palladium catalysis of the Suzuki reaction in water using microwave heating. , 2002, Organic letters.

[13]  P. Walla,et al.  Scalability of Microwave-Assisted Organic Synthesis. From Single-Mode to Multimode Parallel Batch Reactors , 2003 .

[14]  Sambasivarao Kotha,et al.  Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis , 2002 .

[15]  P. He,et al.  Microwave heating of heterogeneously catalysed Suzuki reactions in a micro reactor. , 2004, Lab on a chip.

[16]  P. He,et al.  Microwave-assisted Suzuki reactions in a continuous flow capillary reactor , 2004 .

[17]  N. Anderson.  Practical Use of Continuous Processing in Developing and Scaling Up Laboratory Processes , 2001 .

[18]  M. Poux,et al.  Acylation and Related Reactions under Microwaves. 5. Development to Large Laboratory Scale with a Continuous-Flow Process1 , 2001 .

[19]  Mark B. Anderson,et al.  Electrophilic tetraalkylammonium nitrate nitration. II. Improved anhydrous aromatic and heteroaromatic mononitration with tetramethylammonium nitrate and triflic anhydride, including selected microwave examples. , 2003, Journal of Organic Chemistry.

[20]  J. Bazureau,et al.  Ecofriendly Fast Synthesis of Hydrophilic Poly(ethyleneglycol)-Ionic Liquid Matrices for Liquid-Phase Organic Synthesis. , 2002 .

[21]  Chao-Jun Li,et al.  Organic reactions in aqueous media , 1997 .

[22]  Oljan Repic,et al.  Large scale microwave-accelerated esterification of carboxylic acids with dimethyl carbonate , 2002 .

[23]  N. Leadbeater,et al.  Transition-metal-free Suzuki-type coupling reactions: scope and limitations of the methodology. , 2003, Journal of Organic Chemistry.

[24]  M. J. Collins,et al.  Automated batch scale-up of microwave-promoted Suzuki and Heck coupling reactions in water using ultra-low metal catalyst concentrations , 2005 .

[25]  C. R. Strauss,et al.  A New Microwave Reactor for Batchwise Organic Synthesis , 1995 .

[26]  K. Luthman,et al.  Efficient large scale microwave assisted Mannich reactions using substituted acetophenones , 2004, Molecular Diversity.

[27]  N. Leadbeater,et al.  Transition-metal-free Suzuki-type coupling reactions. , 2003, Angewandte Chemie.

[28]  Wei Zhang,et al.  A highly efficient microwave-assisted suzuki coupling reaction of aryl perfluorooctylsulfonates with boronic acids. , 2004, Organic letters.

[29]  Y. Gong,et al.  Direct synthesis of unprotected 4-aryl phenylalanines via the Suzuki reaction under microwave irradiation. , 2002, Organic letters.

[30]  Jin‐Heng Li,et al.  Efficient Pd(OAc)2/Pyrimidine Catalytic System for Suzuki-Miyaura Cross-Coupling Reaction , 2005 .

[31]  N. Leadbeater.  Fast, easy, clean chemistry by using water as a solvent and microwave heating: the Suzuki coupling as an illustration. , 2005, Chemical communications.

[32]  J. Alcázar,et al.  Reproducibility across Microwave Instruments: First Example of Genuine Parallel Scale up of Compounds under Microwave Irradiation , 2004 .

[33]  Kabza,et al.  Microwave-induced esterification using heterogeneous acid catalyst in a low dielectric constant medium , 2000, The Journal of organic chemistry.

[34]  P. Grieco.  Organic synthesis in water , 1998 .

[35]  F. Chemat,et al.  Pilot scale continuous microwave dry-media reactor - Part 1 : Design and modeling , 2000 .

[36]  C. R. Strauss,et al.  Development and Application of a Continuous Microwave Reactor for Organic Synthesis , 1994 .

[37]  Jin‐Heng Li,et al.  Dabco as an inexpensive and highly efficient ligand for palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. , 2004, Organic letters.

[38]  J. Hamelin,et al.  Ecofriendly Fast Batch Synthesis of Dioxolanes, Dithiolanes, and Oxathiolanes without Solvent under Microwave Irradiation , 1998 .

[39]  N. Leadbeater,et al.  Rapid and amenable suzuki coupling reaction in water using microwave and conventional heating. , 2003, The Journal of organic chemistry.

[40]  Bhushan M. Khadilkar and,et al.  Microwave-assisted synthesis of room-temperature ionic liquid precursor in closed vessel , 2002 .

[41]  A. Petit,et al.  Application of Focused Microwaves to the Scale-Up of Solvent-Free Organic Reactions , 2000 .

[42]  M. Lemaire,et al.  Aryl-aryl bond formation one century after the discovery of the Ullmann reaction. , 2002, Chemical reviews.

[43]  F. Chemat,et al.  Scale Continuous Microwave Dry‐Media Reactor – Part II: Application to Waxy Esters Production , 2000 .

[44]  J. Desmurs,et al.  Acylation Reactions under Microwaves. 3. Aroylation of Benzene and Its Slightly Activated or Deactivated Derivatives1 , 2000 .

[45]  R. Varma,et al.  Microwave-accelerated Suzuki cross-coupling reaction in polyethylene glycol (PEG) , 2001 .

[46]  Jin‐Heng Li,et al.  Recyclable and reusable Pd(OAc)2/DABCO/PEG-400 system for Suzuki-Miyaura cross-coupling reaction. , 2005, The Journal of organic chemistry.