<i>meta</i>-Selective olefination of fluoroarenes with alkynes using CO<sub>2</sub> as a traceless directing group.
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AbstractOver the last few decades C-H olefination has received significant interest, due to the importance and usefulness of aryl olefins both as synthetic targets and intermediates. While a wide range of <i>ortho</i>-olefination protocols have been developed, only a small number of <i>meta</i>-olefinations are currently available. Importantly, the most common approach to <i>meta</i>-olefination, using a large <i>meta</i>-directing template, is not suitable for substrates such as fluorobenzenes, which cannot be derivatised. We report that the <i>meta</i>-selective olefination of fluoroarenes can be achieved <i>via</i> the use of CO<sub>2</sub> as a traceless directing group, which can be easily installed and removed in a one-pot process. Furthermore, this approach avoids the use of stoichiometric Ag(i)-salts, commonly used in C-H olefinations, and affords complete <i>meta</i>- over <i>ortho</i>/<i>para</i>-regioselectivity.
CitationChemical science, volume 11, issue 16, page 4204-4208
DescriptionFrom Europe PMC via Jisc Publications Router
History: ppub 2020-03-01, epub 2020-03-31
Publication status: Published
Funder: Engineering and Physical Sciences Research Council; Grant(s): EP/L014017/2