131379-17-4Relevant articles and documents
Scalability of microwave-assisted organic synthesis. From single-mode to multimode parallel batch reactors
Stadler, Alexander,Yousefi, Behrooz H.,Dallinger, Doris,Walla, Peter,Van Der Eycken, Erik,Kaval, Nadya,Kappe, C. Oliver
, p. 707 - 716 (2003)
The direct scalability of microwave-assisted organic synthesis (MAOS) in a prototype laboratory-scale multimode microwave batch reactor is investigated. Several different organic reactions have been scaled-up typically from 1 mmol to 100 mmol scale. The transformations include multicomponent chemistries (Biginelli dihydropyrimidine and Kindler thioamide synthesis), transition metal-catalyzed carbon - carbon cross-coupling protocols (Heck and Negishi reactions), solid-phase organic synthesis, and Diels - Alder cycloaddition reactions using gaseous reagents in prepressurized reaction vessels. A range of different solvents (high and low microwave absorbing), Pd catalysts (homogeneous and heterogeneous), and varying reaction times and temperatures have been explored in these investigations. In all cases, it was possible to achieve similar isolated product yields on going from a small scale (ca. 5 mL processing volume) to a larger scale (max 500 mL volume) without changing the previously optimized reaction conditions (direct scalability). The prototype, benchtop multimode microwave reactor used in the present study allows parallel processing in either quartz or PTFE-TFM vessels with maximum operating limits of 300°C and 80 bar of pressure. The system features magnetic stirring in all vessels, complete on-line monitoring of temperature, pressure and microwave power, and the ability to maintain inert or reactive gas atmosphere.
Microwave-assisted Negishi and Kumada cross-coupling reactions of aryl chlorides
Walla, Peter,Kappe, C. Oliver
, p. 564 - 565 (2007/10/03)
Rapid Pd or Ni-catalyzed microwave-accelerated Negishi and Kumada cross-coupling reactions of aryl chlorides in solution and on solid phase are reported.
New chemical synthesis of functionalized arylzinc compounds from aromatic or thienyl bromides under mild conditions using a simple cobalt catalyst and zinc dust
Fillon, Hyacinthe,Gosmini, Corinne,Perichon, Jacques
, p. 3867 - 3870 (2007/10/03)
A new chemical method for the preparation of arylzinc intermediates is described in acetonitrile, on the basis of the activation of aryl bromides by low-valent cobalt species arising from the reduction of cobalt halide by zinc dust. This procedure allows for the synthesis of a variety of functionalized aryl- and thienylzinc species in good to excellent yields. The versatility and the simplicity of that original method represent an alternative to most known procedures.