Convenient protocols for Mizoroki-Heck reactions of aromatic bromides and polybromides with fluorous alkenes of the formula H2CCH(CF2)n-1CF3 (n = 8, 10)

Haw Lih Su, Janos Balogh, Mohammed Al-Hashimi, Dave G. Seapy, Hassan S. Bazzi, John A. Gladysz

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)10058-10069
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number42
DOIs
Publication statusPublished - 2016

    Fingerprint

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this