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Issue 42, 2016
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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)

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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)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(CH[double bond, length as m-dash]CHRfn)m are detected. Thirteen representative examples are hydrogenated (Pd/C, balloon pressure H2), giving Ar(CH2CH2Rfn)m (92% average isolated yield).

Graphical abstract: 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)

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Publication details

The article was received on 08 Sep 2016, accepted on 29 Sep 2016 and first published on 06 Oct 2016


Article type: Paper
DOI: 10.1039/C6OB01980C
Citation: Org. Biomol. Chem., 2016,14, 10058-10069
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    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)

    H. Su, J. Balogh, M. Al-Hashimi, D. G. Seapy, H. S. Bazzi and J. A. Gladysz, Org. Biomol. Chem., 2016, 14, 10058
    DOI: 10.1039/C6OB01980C

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