340157-84-8Relevant academic research and scientific papers
Convenient protocols for Mizoroki-Heck reactions of aromatic bromides and polybromides with fluorous alkenes of the formula H2CCH(CF2)n-1CF3 (n = 8, 10)
Su, Haw-Lih,Balogh, Janos,Al-Hashimi, Mohammed,Seapy, Dave G.,Bazzi, Hassan S.,Gladysz, John A.
, p. 10058 - 10069 (2016)
The fluorous alkenes H2CCHRfn (Rfn = (CF2)n-1CF3; n = 8, 10) undergo the Mizoroki-Heck reaction with a variety of aromatic monobromides and polybromides such as 1,3- and 1,4-C6H4Br2, 1,3,5-C6H3Br3, 1,3,5-C6H3Br2Cl, 1,4-XC6H4Br (X = CF3, Rf8, COCH3, CN, 1,4-OC6H4Br), 1,2-O2NC6H4Br, 5-bromoisoquinoline, 5-bromopyrimidine, 3-bromo-5-methoxypyridine, and 3,5-dibromopyridine (sixteen examples, 78% average isolated yield). Typically, 1.2-2.4 equiv. of alkene are employed per Ar-Br bond, together with Pd(OAc)2 catalyst (4-5 mol%/Ar-Br bond), n-Bu4N+ Br- (0.8-1.0 equiv./Ar-Br bond), NaOAc (1.2-2.4 equiv./Ar-Br bond), and 3 : 1 w/w DMF/THF as solvent (120 °C). No effort is necessary to exclude air or moisture, and reactions may be conducted on >10 g scales. Only E isomers of the products Ar(CHCHRfn)m are detected. Thirteen representative examples are hydrogenated (Pd/C, balloon pressure H2), giving Ar(CH2CH2Rfn)m (92% average isolated yield).
Efficient access to perfluoroalkylated aryl compounds by Heck reaction
Darses, Sylvain,Pucheault, Mathieu,Genet, Jean-Pierre
, p. 1121 - 1128 (2007/10/03)
Efficient introduction of perfluorinated tails onto aromatic rings has been achieved by Heck reaction between perfluoroalkenes and arenediazonium salts, catalysed by palladium acetate. Subsequent transition metal catalysed hydrogenation of the double bond afforded a large variety of aromatic compounds bearing an affinity for fluorous solvents. Formation of perfluoroalkylated phosphane ligands and their use in palladium-catalysed coupling between potassium trifluoro(vinyl)borates and diazonium salts is also described, allowing an easy separation and recycling of the catalytic system.
