6145-10-4Relevant academic research and scientific papers
Stille cross-coupling of activated alkyltin reagents under "ligandless" conditions
Herve, Agnes,Rodriguez, Alain L.,Fouquet, Eric
, p. 1953 - 1956 (2007/10/03)
(Chemical Equation Presented) Monoalkyltins activated by a fluoride source are shown to be as reactive as their vinyl or aryl homologues in the Stille coupling reaction, thus providing an easy entry into the pallado-catalyzed formation of Csp3-Csp2 bonds. In addition to this uncommon reactivity, this methodology holds several advantages such as (i) a quantitative preparation of stable and easy to handle alkyltin reagents 2, (ii) a simplified coupling procedure without any phosphine added ligand under neutral conditions, and (iii) a facile purification step of the organic products from the inorganic nontoxic tin byproducts.
Strategy and design in fluorous phase immobilization: A systematic study of the effect of 'pony tails' (CH2)3(CF2)n-1CF3 on the partition coefficients of benzenoid compounds
Rocaboy, Christian,Rutherford, Drew,Bennett, Byron L.,Gladysz
, p. 596 - 603 (2007/10/03)
Fluorous solvents commonly exhibit temperature-dependent miscibilities with organic solvents. Thus, catalysts and reagents that have high affinities for fluorous solvents can be used in protocols that combine the advantages of one-phase chemistry (higher temperature) and biphase product separation (lower temperature). The high-yield conversion of benzaldehydes (via Wittig and hydrogenation reactions) to alkylbenzenes with one to three 'pony tails' (CH2)3(CF2)n-1CF3 (n = 6, 8, 10) is described. The toluene-CF3C6F11 partition coefficients show that three pony tails are necessary to achieve a high degree of fluorous phase immobilization. Copyright
Copper catalyzed Grignard cross-coupling reaction with β-perfluoroalkyl-substituted alkyl halides
Shimizu, Rie,Yoneda, Eiichi,Fuchikami, Takamasa
, p. 5557 - 5560 (2007/10/03)
Coupling reaction of β-perfluoroalkyl-substituted alkyl halides with Grignard reagents such as phenyl-, vinyl-, allyl-, benzyl-, and alkyl-magnesium halides was catalyzed by copper salts or complexes to give the corresponding cross-coupling products in good yields. α,ω-Diiodoalkane bearing a polyfluoroalkylene moiety also reacted with 2 equiv. of Grignard reagent in the presence of copper catalyst to given α,ω-bi-functionalized product.
