AI Article Synopsis
- The study discusses a method for allylic C-H acyloxylation of terminal alkenes using 4-nitrobenzoic acid, which is facilitated by a special palladium catalyst.
- The addition of AgCO and 4-nitrobenzoic acid boosts the catalyst's effectiveness, allowing for high selectivity and a variety of substrates with low amounts of palladium.
- This method successfully transformed ethyl 7-octenoate into ethyl 6,8-dihydroxyoctanoate, an important intermediate in the synthesis of ()-α-lipoic acid.
Article Abstract
An allylic C-H acyloxylation of terminal alkenes with 4-nitrobenzoic acid was assisted by a bidentate-sulfoxide-ligated palladium catalyst combined with 1,4-benzoquinone and AgCO under mild reaction conditions. The catalytic activity was remarkably enhanced by AgCO as an additive and 4-nitrobenzoic acid as a carboxylate source; both components were essential to exhibiting high catalytic activity, high branch selectivity, and a wide substrate scope with low loading of the palladium catalyst. Branch-selective allylic acyloxylation of ethyl 7-octenoate () gave the product which was led to ethyl 6,8-dihydroxyoctanoate (), a useful synthetic intermediate of ()-α-lipoic acid.
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| http://dx.doi.org/10.1021/acs.orglett.1c02406 | DOI Listing |
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