More Nagnath Y, Rist Paige A, Gupta Aniket, Davies Paul W
School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, U.K.
Org Lett. 2024 Sep 13;26(36):7713-7717. doi: 10.1021/acs.orglett.4c02853. Epub 2024 Aug 29.
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.
引入亚磺酰化炔丙基羧酸盐以研究硫取代对金催化的炔烃活化途径的影响。区域发散性金催化的重排和吲哚捕获反应在温和条件下进行,得到带有亚磺酰化()-烯醇羧酸盐基序的功能化吲哚产物。涉及1,2-和1,3-羧酸盐迁移的途径均可选择性实现,在每种情况下,吲哚均以与亚磺酰基呈1,4关系的方式添加。高选择性受催化剂体系、抗衡离子和羧酸盐基团的影响。