Photocatalytic transfer hydrogenolysis of aromatic ketones using alcohols

A mild method of photocatalytic deoxygenation of aromatic ketones to alkyl arenes was developed, which utilized alcohols as green hydrogen donors. No hydrogen evolution during this transformation suggested a mechanism of direct hydrogen transfer from alcohols. Control experiments with additives indi...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 22; no. 12; pp. 382 - 388
Main Authors Li, Hongji, Gao, Zhuyan, Lei, Lijun, Liu, Huifang, Han, Jianyu, Hong, Feng, Luo, Nengchao, Wang, Feng
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2020
Royal Society of Chemistry
Subjects
Additives
Alcohol
Alcohols
Aromatic compounds
Catalysts
Chemistry
Chemistry, Multidisciplinary
Deoxygenation
Donors (electronic)
Green & Sustainable Science & Technology
Green chemistry
Green hydrogen
Hydrogen
Hydrogen evolution
Hydrogenolysis
Ketones
Photocatalysis
Photocatalysts
Physical Sciences
Science & Technology
Science & Technology - Other Topics
Titanium dioxide
OXIDATION
TRANSFORMATION
FORMIC-ACID
PALLADIUM
REDUCTION
TEMPERATURE
BENZYLIC ALCOHOLS
CATALYZED TRANSFER HYDROGENOLYSIS
SELECTIVE DEOXYGENATION
EFFICIENT
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Summary:A mild method of photocatalytic deoxygenation of aromatic ketones to alkyl arenes was developed, which utilized alcohols as green hydrogen donors. No hydrogen evolution during this transformation suggested a mechanism of direct hydrogen transfer from alcohols. Control experiments with additives indicated the role of acid in transfer hydrogenolysis, and catalyst characterization confirmed a larger number of Lewis acidic sites on the optimal Pd/TiO 2 photocatalyst. Hence, a combination of hydrogen transfer sites and acidic sites may be responsible for efficient deoxygenation without additives. The photocatalyst showed reusability and achieved selective reduction in a variety of aromatic ketones. Photocatalytic deoxygenation of aromatic ketones to alkyl arenes was developed on Pd/TiO 2 using alcohols as green hydrogen donors.
Bibliography:Feng Wang received his B.Sc. from Zhengzhou University (1999) and Ph.D. from Dalian Institute of Chemical Physics, the Chinese Academy of Sciences (2005). He spent 2005-2006 as a postdoctoral fellow at the University of California, Berkeley in the USA and 2006-2009 at Hokkaido University, Catalysis Research Center in Japan. He serves as a full professor and an independent PI at Dalian Institute of Chemical Physics (2009), a joint professor in the State Key Laboratory of Catalysis at DICP (2013), and is the director of the Division of Biomass Conversion & Bio-Energy at DICP (2018 to present). He served as the Cheung Kong Professor at Dalian University of Technology in 2016. His current research focuses on heterogeneous catalysis and biomass conversion.
Electronic supplementary information (ESI) available. See DOI
10.1039/d0gc00732c
ISSN:1463-9262
1463-9270
DOI:10.1039/d0gc00732c