Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 2-3, Pages 341-347Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201200832
Keywords
deoxygenation; hydrogenolysis; palladium; reduction; polymethylhydrosiloxane (PMHS); silanes
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Funding
- National Natural Science Foundation of China [21173064, 51203037]
- Zhejiang Provincial Natural Science Foundation of China [Q12B020037]
- Program for Excellent Young Teachers in Hangzhou Normal University (HNUEYT)
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A simple method has been developed for the reductive deoxygenation of aromatic ketones and benzylic alcohols in the presence of polymethylhydrosiloxane (PMHS). The reductive deoxygenation of aromatic ketones and benzylic alcohols, including secondary alcohols, to the corresponding methylene hydrocarbons has been achieved in good to excellent yields using palladium chloride (PdCl2) as catalyst and PMHS as hydride source. Such deoxygenations were successfully with aryl alkyl ketones and diaryl ketones, as exemplified by the reductive deoxygenation of acetophenone and benzopheneone, respectively. The corresponding benzylic alcohols and secondary alcohol analogues could also be converted into their respective methylene hydrocarbons by the PdCl2/PMHS system.
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