Catalytic transformation of aliphatic alcohols to corresponding esters in O2 under neutral conditions using visible-light irradiation

Xiao, Qi, Liu, Zhe, Bo, Arixin, Zavahir, Sifani, Sarina, Sarina, Bottle, Steven, Riches, James D., & Zhu, Huaiyong (2015) Catalytic transformation of aliphatic alcohols to corresponding esters in O2 under neutral conditions using visible-light irradiation. Journal of the American Chemical Society, 137(5), pp. 1956-1966.

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Abstract

Selective oxidation of aliphatic alcohols under mild and base-free conditions is a challenging process for organic synthesis. Herein, we report a one-pot process for the direct oxidative esterification of aliphatic alcohols that is significantly enhanced by visible-light irradiation at ambient temperatures. The new methodology uses heterogenerous photocatalysts of gold–palladium alloy nanoparticles on a phosphate-modified hydrotalcite support and molecular oxygen as a benign oxidant. The alloy photocatalysts can absorb incident light, and the light-excited metal electrons on the surface of metal nanoparticles can activate the adsorbed reactant molecules. Tuning the light intensity and wavelength of the irradiation can remarkably change the reaction activity. Shorter wavelength light (<550 nm) drives the reaction more efficiently than light of longer wavelength (e.g., 620 nm), especially at low temperatures. The phosphate-exchanged hydrotalcite support provides sufficient basicity (and buffer) for the catalytic reactions; thus, the addition of base is not required. The photocatalysts are efficient and readily recyclable. The findings reveal the first example of using “green” oxidants and light energy to drive direct oxidative esterification of aliphatic alcohols under base-free, mild conditions.

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ID Code: 90648
Item Type: Journal Article
Refereed: Yes
Keywords: photocatalysis
DOI: 10.1021/ja511619c
ISSN: 1520-5126
Subjects: Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > MACROMOLECULAR AND MATERIALS CHEMISTRY (030300) > Physical Chemistry of Materials (030304)
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Schools > School of Earth, Environmental & Biological Sciences
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Funding:
Facilities: Science and Engineering Centre
Copyright Owner: Copyright 2015 American Chemical Society
Copyright Statement: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/ja511619c
Deposited On: 23 Nov 2015 00:24
Last Modified: 02 Sep 2016 08:27

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