Effect of chiral ionic liquids on palladium-catalyzed Heck arylation of 2,3-dihydrofuran was written by Roszak, Rafal;Trzeciak, Anna M.;Pernak, Juliusz;Borucka, Nina. And the article was included in Applied Catalysis, A: General in 2011.SDS of cas: 65350-59-6 This article mentions the following:
A relatively small amount of IL (IL = ionic liquid) can dramatically affect conversion in the Heck arylation of 2,3-dihydrofuran with iodobenzene, catalyzed by Pd(OAc)2 in DMF as a solvent. In all reactions, 2-phenyl-2,3-dihydrofuran (3) was obtained as the main product, and conversion increased even up to 10 times when pyridinium salts with 1-butyl-4-methylpyridinium cation were applied. In a 1:1 mixture of DMF and H2O as solvent, the addition of ILs led to a remarkable deactivation of the catalyst, and this effect was most visible in the presence of imidazolium salts containing a 1-butyl-3-methylimidazolium cation. The influence of the anionic part of ILs on the reaction course was tested using a series of morpholinium salts and, depending on the anion, conversion varied from 0.4% to even 100%. When morpholinium salts with chiral anions were used, e.e. values of up to 10% were obtained, which is the highest value for the Heck reaction involving IL as a chirality source. In the experiment, the researchers used many compounds, for example, 1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6SDS of cas: 65350-59-6).
1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6) belongs to pyridine derivatives. Pyridine has a conjugated system of six 闂?electrons that are delocalized over the ring. The molecule is planar and, thus, follows the H闂佹椿浜滈妴鍗l criteria for aromatic systems. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.SDS of cas: 65350-59-6