title: Convenient protocols for Mizoroki-Heck reactions of aromatic bromides and polybromides with fluorous alkenes of the formula H2C[double bond, length as m-dash]CH(CF2)n-1CF3(n = 8, 10).
abstract: The fluorous alkenes H2C[double bond, length as m-dash]CHRfn(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)2catalyst (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(CH[double bond, length as m-dash]CHRfn)mare detected. Thirteen representative examples are hydrogenated (Pd/C, balloon pressure H2), giving Ar(CH2CH2Rfn)m(92% average isolated yield).
authors.affiliation: Department of Chemistry, Texas A&M University at Qatar, P.O. Box 23874, Doha, Qatar. bazzi@tamu.edu.
authors.forename: Haw-Lih
authors.initials: HL
authors.lastname: Su
authors.affiliation: Department of Chemistry, Texas A&M University at Qatar, P.O. Box 23874, Doha, Qatar. bazzi@tamu.edu.
authors.forename: Janos
authors.initials: J
authors.lastname: Balogh
authors.affiliation: Department of Chemistry, Texas A&M University at Qatar, P.O. Box 23874, Doha, Qatar. bazzi@tamu.edu.
authors.forename: Mohammed
authors.initials: M
authors.lastname: Al-Hashimi
authors.affiliation: Department of Chemistry, Texas A&M University at Qatar, P.O. Box 23874, Doha, Qatar. bazzi@tamu.edu.
authors.forename: Dave G
authors.initials: DG
authors.lastname: Seapy
authors.affiliation: Department of Chemistry, Texas A&M University at Qatar, P.O. Box 23874, Doha, Qatar. bazzi@tamu.edu.
authors.forename: Hassan S
authors.initials: HS
authors.lastname: Bazzi
authors.affiliation: Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, Texas 77842-3012, USA. gladysz@mail.chem.tamu.edu.
authors.forename: John A
authors.identifier: http://orcid.org/0000-0002-7012-4872
authors.initials: JA
authors.lastname: Gladysz