10.1002/anie.201711531
Angewandte Chemie International Edition
COMMUNICATION
3). Time-course reaction also supports the above-mentioned
mechanism (see Scheme S1 of Supporting Information). However,
our reaction gave a much wider substrate scope compared to
Yang’s metal-free system (limited to benzylic diols only). The
efficient cleavage of most of our substrates cannot proceed
without Ag(I) catalyst. This implies the efficiency of silver in
activation of oxygen.9
Acknowledgements
We are grateful to the Canada Research Chair Foundation (to
C.-J. L.), the Canadian Foundation for Innovation, FRQNT Centre
in Green Chemistry and Catalysis, and the Natural Science and
Engineering Research Council of Canada for support of our
research. Dr. Z.-Z. Zhou is grateful for the support from China
Scholarship Council (CSC) and Scholarship Council of Southern
Medical University. Dr. L. Lv is grateful for the support from
National Postdoctoral Program for Innovative Talents
(BX201700110) and China Postdoctoral Science Foundation
Funded Project (No. 2017M623270).
Keywords: 1,2-diol • aerobic oxidative cleavage • carboxylic
acids • selectivity • silver catalyst
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Figure 2. Scaling-up of the aerobic diol oxidative cleavage
Scheme 2. Isotope labelling experiment
Scheme 3. Aerobic oxidative cleavage of benzil
In summary, we have developed a widely adaptable and
selective aerobic oxidative cleavage of 1,2-diols. The reaction
proceeds under mild conditions with readily available catalyst that
exhibits high efficiency. A wide scope of substrates including
natural products have been successfully cleaved by the method
to generate the corresponding carboxylic acids. Further
applications of silver catalyst towards other oxidation processes
are underway in our lab.
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