ArticleACS catalysis2022
Steric Shielding Effects Induced by Intramolecular C-H⋯O Hydrogen Bonding: Remote Borylation Directed by Bpin Groups.
Article in ACS catalysis, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
4 citing papers in PubMed.
- Balancing Reactivity, Regioselectivity, and Product Stability in Ir-Catalyzed Ortho-C-H Borylations of Anilines by Modulating the Diboron Partner.Organic letters · 2024Article
- A Hydrazone Ligand for Iridium-Catalyzed C-H Borylation: Enhanced Reactivity and Selectivity for Fluorinated Arenes.Organometallics · 2024Article
- Trialkoxysilane-Induced Iridium-Catalyzed para-Selective C-H Bond Borylation of Arenes.Nature communications · 2024Article
- Transition metal-catalyzed remote C─H borylation: An emerging synthetic tool.Science advances · 2023Review
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
Regioselectivities in catalytic C-H borylations (CHBs) have been rationalized using simplistic steric models and correlations with nuclear magnetic resonance (NMR) chemical shifts. However, regioselectivity can be significant for important substrate classes where none would be expected from these arguments. In this study, intramolecular hydrogen bonding (IMHB) can lead to steric shielding effects that can direct Ir-catalyzed CHB regiochemistry. Bpin (Bpin = pinacol boronic ester)/arene IMHB can promote remote borylations of N-borylated anilines, 2-amino-N-alkylpyridine, tetrahydroquinolines, indoles, and 1-borylated naphthalenes. Experimental and computational studies support molecular geometries with the Bpin orientation controlled by a C-H⋯O IMHB. IMHB-directed remote CHB appeared operative in the C6 borylation of 3-aminoindazole (seven-membered IMHB) and C6 borylation of an osimertinib analogue where a pyrimidine IMHB creates the steric shield. This study informs researchers to evaluate not only inter- but also intramolecular noncovalent interactions as potential drivers of remote CHB regioselectivity.
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Registered trials
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