916576-33-5Relevant academic research and scientific papers
Efficient palladium(II) catalysis under air. Base-free oxidative heck reactions at room temperature or with microwave heating
Lindh, Jonas,Enquist, Per-Anders,Pilotti, Ake,Nilsson, Peter,Larhed, Mats
, p. 7957 - 7962 (2007)
(Figure Presented) Scope and limitations of the base-free oxidative Heck reaction with arylboronic acids have been explored. Under our conditions, the dmphen-palladium(II)-catalyzed arylation proceeded with air or p-benzoquinone as reoxidants of palladium(0). We found that ambient temperature and mild aerobic conditions allow for the use of substrates sensitive to palladium(II)-catalyzed oxidation. Oxidative Heck couplings, employing different arylboronic acids, were smoothly and regioselectively conducted with both electron-rich and electron-poor olefins, providing high yields even with disubstituted butyl methacrylate, sensitive acrolein, and a vinylboronate ester. Controlled microwave processing was used to reduce reaction times from hours to minutes both in small scale and in 50 mmol scale batch processes.
Bipyridine-modulated palladium-catalyzed oxidative heck-type reactions of arylboronic acids with olefins
Hsu, Chien-Ming,Li, Chih-Bin,Sun, Chia-Hsing
experimental part, p. 873 - 880 (2010/08/19)
We have demonstrated that 4,4′-dimethyl 2,2′-bipyridine as ligand for Pd(II) catalysts was very efficient for oxidative Heck-type coupling reaction of arylboronic acids with olefins in DMA or CH3CN under atm air at 80 °C. The presence of chelated bipyridine ligand isindispensable to achieve high reaction yields and to suppress the formation of biphenyl as homocoupled byproduct.
Mass spectrometric screening of enantioselective Diels-Alder reactions
Teichert, Antje,Pfaltz, Andreas
experimental part, p. 3360 - 3362 (2009/02/07)
(Chemical Equation Presented) A rapid cat. scan: Mass spectrometric monitoring of reaction intermediates of the retro-Diels-Alder reaction has allowed the rapid screening of catalysts for enantioselective Diels-Alder reactions (see scheme). Copper catalysts as well as metal-free organocatalysts were tested. A protocol for the simultaneous screening of catalyst mixtures has also been developed, which offers new possibilities for high-throughput catalyst development.
