Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 37, Pages 12037-12040Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b07411
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Funding
- 973 Program [2011CB808600, 2012CB725302, 2013CB834804]
- National Natural Science Foundation of China [21390400, 21272180, 21302148, 2109343, 21402217]
- Research Fund for the Doctoral Program of Higher Education of China [20120141130002]
- Ministry of Science and Technology of China [2012YQ120060]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT1030]
- Program of Introducing Talents of Discipline to Universities of China (111 Program)
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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 beta-alkyl styrenes and their derivatives with water under external-oxidant-free conditions by utilizing the synergistic effect of photo catalysis 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.
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