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Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols on Pd/TiO 2 : A Shortcut to ( S )‐(+)‐Lavandulol
Author(s) -
Takada Yuki,
Caner Joaquim,
Kaliyamoorthy Selvam,
Naka Hiroshi,
Saito Susumu
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704099
Subject(s) - hydrogenolysis , allylic rearrangement , chemistry , photocatalysis , olefin fiber , steric effects , stereoselectivity , catalysis , alcohol , stoichiometry , oxide , organic chemistry , photochemistry
We report herein a regio‐ and stereoselective photocatalytic hydrogenolysis of allylic alcohols to form unsaturated hydrocarbons employing a palladium(II)‐loaded titanium oxide; the reaction proceeds at room temperature under light irradiation without stoichiometric generation of salt wastes. Olefin and saturated alcohol moieties tolerated the reaction conditions. Hydrogen atoms were selectively incorporated into less sterically congested carbons of the allylic functionalities. This protocol allowed a short‐step synthesis of ( S )‐(+)‐lavandulol from ( R )‐(−)‐carvone by avoiding otherwise necessary protection/deprotection steps.