Lewis acid catalysis by lanthanide complexes with tris(perfluorooctanesulfonyl)methide ponytails in fluorous recyclable phase

A Palladium/Perfluoroalkylated Pyridine Catalyst for Sonogashira Reaction of Aryl Bromides and Chlorides in a Fluorous Biphasic System

“…The perfluorodecalin/toluene partition coefficients were determined by GC or ICP according to a previously reported method. [26,27] These reflect relative as opposed to absolute solubilities and are summarized in Table 1. In pyridine ligand, two R f8 pony tails give high fluorous phase affinities (coefficients 99.8:0.2), allowing essentially quantitative recovery.…”

Fluorous Organometallic Chemistry

“…Reaction of 1,6-diiodododecafluorohexane with ZnEt 2 generates an unusual bisperfluoroalkyl-bridged dizinc species, [(solv) 2 Zn(μ 2 -C 6 F 12 )Zn(solv) 2 ] (solv ¼ MeCN, 1,3-dimethyl-3,4,5,6-tetrahydro-1(1H)-pyrimidinone); the latter has been used as a transfer reagent for the perfluoroalkyl chain to form perfluoro-bridged diaryls in the presence of CuCl [106]. Some experimental details for the isolation of the highly active Lewis acid scandium and ytterbium(III) tris(perfluoroalkylsulfonyl) methide catalysts have been reported [107][108][109][110]. The reaction of fluorous-1,5-diphosphinopentanes (IX) with Pd(O 2 CCF 3 ) 2 in benzotrifluoride at elevated temperatures afforded a small series of palladium(II) PCP pincers complexes ( Fig.…”

Development of Industrial Reaction Processes Using Fluorous Lewis Acid Catalysts

“…We have reported that the fluorous Lewis acid catalysts were useful and recyclable in carbon -carbon bond forming reactions such as Diels -Alder reaction, Mukaiyama aldol reaction [8], and Friedel -Crafts acylation [9]. In particular, Friedel -Crafts acylation generally needs an equimolar or more amount of catalyst such as aluminum chloride.…”