Volume 23, Issue 71 p. 18025-18032
Full Paper

Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols on Pd/TiO2: A Shortcut to (S)-(+)-Lavandulol

Dr. Yuki Takada

Dr. Yuki Takada

Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan

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Dr. Joaquim Caner

Dr. Joaquim Caner

Research Center for Materials Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan

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Dr. Selvam Kaliyamoorthy

Dr. Selvam Kaliyamoorthy

Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan

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Prof.Dr. Hiroshi Naka

Prof.Dr. Hiroshi Naka

Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan

Research Center for Materials Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan

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Prof. Dr. Susumu Saito

Corresponding Author

Prof. Dr. Susumu Saito

Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan

Research Center for Materials Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan

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First published: 03 October 2017
Citations: 15

Graphical Abstract

Synthetic usefulness of regio- and stereoselective photocatalytic hydrogenolysis of various allylic alcohols to unsaturated hydrocarbons by using PdII/TiO2(P25) was demonstrated; the hydrogenolysis proceeds at room temperature under light irradiation without stoichiometric generation of salt waste, allowing a step-economical synthesis of (S)-(+)-lavandulol by avoiding otherwise necessary protection/deprotection steps.

Abstract

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.

Conflict of interest

The authors declare no conflict of interest.