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J Am Chem Soc. 2016 Sep 21;138(37):12037-40. doi: 10.1021/jacs.6b07411. Epub 2016 Sep 9.

Anti-Markovnikov Oxidation of β-Alkyl Styrenes with H2O as the Terminal Oxidant.

Author information

1
College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University , Wuhan, Hubei 430072, P. R. China.
2
Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences , Lanzhou 730000, P. R. China.

Abstract

Oxygenation of alkenes is one of the most straightforward routes for the construction of carbonyl compounds. Wacker oxidation provides a broadly useful strategy to convert the mineral oil into higher value-added carbonyl chemicals. However, the conventional Wacker chemistry remains problematic, such as the poor activity for internal alkenes, the lack of anti-Markovnikov regioselectivity, and the high cost and chemical waste resulted from noble metal catalysts and stoichiometric oxidant. Here, we describe an unprecedented dehydrogenative oxygenation of β-alkyl styrenes and their derivatives with water under external-oxidant-free conditions by utilizing the synergistic effect of photocatalysis and proton-reduction catalysis that can address these challenges. This dual catalytic system possesses the single anti-Markovnikov selectivity due to the property of the visible-light-induced alkene radical cation intermediate.

PMID:
27595272
DOI:
10.1021/jacs.6b07411

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