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A radical approach to the copper oxidative addition problem: Trifluoromethylation of bromoarenes

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Science  01 Jun 2018:
Vol. 360, Issue 6392, pp. 1010-1014
DOI: 10.1126/science.aat4133

Arenes get a light boost onto copper

Insertion of palladium into an aryl halide bond is the first step in numerous variants of cross-coupling chemistry used to make carbon-carbon bonds. Copper is an appealing alternative catalyst for such reactions because of its abundance and downstream reactivity profile. However, this preliminary step, termed oxidative addition, is often prohibitively slow for the cheaper metal. Le et al. report a photocatalytic way around this problem. A photoredox catalyst paired with a silane can activate aryl bromides to react with copper, likely via aryl radicals. The copper in this case then catalyzes trifluoromethylation of the arenes.

Science, this issue p. 1010