ArticleChemical science2020
Regiocontrol in the oxidative Heck reaction of indole by ligand-enabled switch of the regioselectivity-determining step.
Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Elucidating Ligand-Dependent Selectivities in Pd-Catalyzed C-H Activations.Angewandte Chemie (International ed. in English) · 2025Article
- Metal-free molecular editing of indole via tandem reaction: Access to 2-aryl-3-aryldiazenylindole for theranostic applications.iScience · 2025Article
- From Mono-Accounts of chemical research · 2025Review
- Iridium/Silver-Catalyzed H/D Exchange for Perdeuteration of Indoles and Site-Selective Deuteration of Carbazoles: Application in Late-Stage Functionalization.The Journal of organic chemistry · 2025Article
- Ligand-Controlled NondirectedACS catalysis · 2024Article
- Iridium catalysed C2 site-selective methylation of indoles using a pivaloyl directing group through weak chelation-assistance.RSC advances · 2023Article
- Ligand switchable site selectivity in C-H alkenylation of thiophenes by turnover-limiting step control.Chemical communications (Cambridge, England) · 2021Article
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Authors and funding
4 authors.
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Abstract
Efficient control of regioselectivity is a key concern in transition-metal-catalyzed direct C-H functionalization reactions. Various strategies for regiocontrol have been established by tuning the selectivity of the C-H activation step as a common mode. Herein, we present our study on an alternative mode of regiocontrol, in which the selectivity of the C-H activation step is no longer a key concern. We found that, in a reaction where the C-H activation step exhibits a different regio-preference from the subsequent functionalization step, a ligand-enabled switch of the regioselectivity-determining step could provide efficient regiocontrol. This mode has been exemplified by the Pd(ii)-catalyzed aerobic oxidative Heck reaction of indoles, in which a ligand-controlled C3-/C2-selectivity was achieved for the first time by the development of sulfoxide-2-hydroxypyridine (SOHP) ligands.
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