Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 10, Pages 1684-1690Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700036
Keywords
aerobic oxidation; copper catalysis; hydroxysulfenylation; lactonization; unsaturated carboxylic acids
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Funding
- National Natural Science Foundation of China [21102071, 21472082]
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A copper(II) acetate-catalyzed aerobic thiolation of C=C double bonds, oxygenation, and intramolecular cyclization reactions of unsaturated carboxylic acids with thiols has been explored. The reaction proceeds through a new hydroxysulfenylation-initiated lactonization pathway with carboxyl as electrophilic group, which provides an efficient access to assembly highly valuable thio-substituted lactone derivatives with good yields under mild conditions. Several control experiments, as well as an isotope labelling experiment disclose that oxygen acts as both oxidant and reactant being transferred into the final product. The mechanistic studies support the discovery of a new strategy through difunctionalization of alkenes based on unsaturated carboxylic acids to construct the diversely substituted lactones.
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