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Regiodivergent Gold-Catalyzed Rearrangement–Addition Reactions of Sulfenylated Propargylic Carboxylates with Indoles

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide 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 ( Z )-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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c02853

Authors: Nagnath Y. More, Paige A. Rist, Aniket Gupta, Paul W. Davies

Institution: University of Birmingham

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Engineering and Physical Sciences Research Council, H2020 Marie Skłodowska-Curie Actions