Anti-Markovnikov Oxidation of β-Alkyl Styrenes with H2O as the Terminal Oxidant.
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.
College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University , Wuhan, Hubei 430072, P. R. China.
Guoting
G
Zhang
College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University , Wuhan, Hubei 430072, P. R. China.
Xia
X
Hu
College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University , Wuhan, Hubei 430072, P. R. China.
Chien-Wei
CW
Chiang
College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University , Wuhan, Hubei 430072, P. R. China.
Hong
H
Yi
College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University , Wuhan, Hubei 430072, P. R. China.
Pengkun
P
Pei
College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University , Wuhan, Hubei 430072, P. R. China.
Atul K
AK
Singh
College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University , Wuhan, Hubei 430072, P. R. China.|Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences , Lanzhou 730000, P. R. China.
Aiwen
A
Lei