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The Heck Reaction of Allylic Alcohols Catalyzed by Palladium Nanoparticles in Water: Chemoenzymatic Synthesis of ( R )‐(−)‐Rhododendrol
Author(s) -
Boffi Alberto,
Cacchi Sandro,
Ceci Pierpaolo,
Cirilli Roberto,
Fabrizi Giancarlo,
Prastaro Alessandro,
Niembro Sandra,
Shafir Alexandr,
Vallribera Adelina
Publication year - 2011
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201000260
Subject(s) - heck reaction , palladium , allylic rearrangement , catalysis , chemistry , aryl , phosphine , enantioselective synthesis , organic chemistry , nanoparticle , combinatorial chemistry , covalent bond , materials science , nanotechnology , alkyl
The use of phosphine‐free perfluoro‐tagged palladium nanoparticles immobilized on fluorous silica gel (FSG), either through fluorous–fluorous interactions or covalent bonding, in the Heck reaction of aryl iodides with allylic alcohols under aerobic conditions in water is described. 4‐(4‐Methoxyphenyl)‐butan‐2‐one, an important fine chemical, is readily accessed by this procedure. A two‐step one‐pot process, involving a Heck reaction followed by an enantioselective enzyme‐catalyzed reduction, to form chiral alcohols is applied to the synthesis of ( R )‐(−)‐rhododendrol. The palladium catalysts can be recycled several times, both in the Heck reaction and in the one‐pot chemoenzymatic process.