Harnessing Applied Potential: Selective β‑Hydrocarboxylation of Substituted Olefins

The construction of carboxylic acid compounds in a selective fashion from low value materials such as alkenes remains a long-standing challenge to synthetic chemists. In particular, β-addition to styrenes is underdeveloped. Herein we report a new electrosynthetic approach to the selective hydrocarbo...

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Veröffentlicht in:Journal of the American Chemical Society 2020-01, Vol.142 (4), p.1780-1785
Hauptverfasser: Alkayal, Anas, Tabas, Volodymyr, Montanaro, Stephanie, Wright, Iain A, Malkov, Andrei V, Buckley, Benjamin R
Format: Artikel
Sprache:eng
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Zusammenfassung:The construction of carboxylic acid compounds in a selective fashion from low value materials such as alkenes remains a long-standing challenge to synthetic chemists. In particular, β-addition to styrenes is underdeveloped. Herein we report a new electrosynthetic approach to the selective hydrocarboxylation of alkenes that overcomes the limitations of current transition metal and photochemical approaches. The reported method allows unprecedented direct access to carboxylic acids derived from β,β-trisubstituted alkenes, in a highly regioselective manner.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b13305