AI Article Synopsis
- Researchers explored how adding sulfur to propargylic carboxylates affects gold-catalyzed reactions involving alkynes.
- These reactions lead to the creation of functionalized indole products under mild conditions using a regiodivergent approach.
- Selective carboxylate migrations (both 1,2 and 1,3) were achieved, with indole attaching in a 1,4 position relative to the sulfenyl group, influenced by factors like the catalyst system and counterion.
Article Abstract
Sulfenylated propargylic carboxylates were introduced to investigate the influence of sulfur substitution in gold-catalyzed alkyne activation pathways. Regiodivergent gold-catalyzed rearrangement and indole capture reactions proceed under mild conditions to give functionalized indole products bearing sulfenylated ()-enol carboxylate motifs. Pathways involving both 1,2- and 1,3-carboxylate migrations are achieved selectively, with indole being added in a 1,4 relationship to the sulfenyl group in each case. High levels of selectivity are influenced by the catalyst system, counterion, and carboxylate group.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11406574 | PMC |
| http://dx.doi.org/10.1021/acs.orglett.4c02853 | DOI Listing |
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