ArticleJournal of the American Chemical Society2018
Rhodium-Catalyzed Regioselective Silylation of Alkyl C-H Bonds for the Synthesis of 1,4-Diols.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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22 citing papers in PubMed, 86 citations in OpenAlex.
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- Iridium-Catalyzed, Site-Selective Silylation of Secondary C(spJournal of the American Chemical Society · 2023Article
- Inorganometallics (Transition Metal-Metalloid Complexes) and Catalysis.Chemical reviews · 2022Review
- Catalytic Net Oxidative C-C Activation and Silylation of Cyclopropanols with a Traceless Acetal Directing Group.ACS catalysis · 2022Article
- Exploration of the Mechanism of the Dimerization of Hydroxymethylsilanetriol Using Electronic Structure Methods.ACS omega · 2022Article
- Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(spChemical reviews · 2021Review
- HCoordination chemistry reviews · 2021Article
- Visible light-driven Giese reaction with alkyl tosylates catalysed by nucleophilic cobalt.RSC advances · 2021Article
- Site-selective functionalization of remote aliphatic C-H bondsChemical science · 2020Review
- Late-Stage Diversification of Natural Products.ACS central science · 2020Review
- Ligand-Enabled β-Methylene C(spAngewandte Chemie (International ed. in English) · 2020Article
- Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2020Article
- Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand.Angewandte Chemie (International ed. in English) · 2020Article
- Visible-Light-Induced Alkoxyl Radicals Enable α-C(spiScience · 2020Article
- Tools for Prescreening the Most Active Sites on Ir and Rh Clusters toward C-H Bond Cleavage of Ethane: NBO Charges and Wiberg Bond Indexes.ACS omega · 2019Article
- Hemilabile Benzyl Ether Enables γ-C(spJournal of the American Chemical Society · 2019Article
- Iridium-Catalyzed Silylation of Unactivated C-H Bonds.Tetrahedron · 2019Article
- Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.Journal of the American Chemical Society · 2019Article
- UmpolungACS catalysis · 2019Article
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3 authors at 1 institution in 1 country.
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Abstract
A rhodium-catalyzed intramolecular silylation of alkyl C-H bonds has been developed that occurs with unusual selectivity for the C-H bonds located δ to the oxygen atom of an alcohol-derived silyl ether over typically more reactive C-H bonds more proximal to the same oxygen atom. (Hydrido)silyl ethers, generated in situ by dehydrogenative coupling of tertiary alcohols with diethylsilane, undergo regioselective silylation at a primary C-H bond δ to the hydroxyl group in the presence of [(Xantphos)Rh(Cl)] as catalyst. Oxidation of the resulting 6-membered oxasilolanes generates 1,4-diols. This silylation and oxidation sequence provides an efficient method to synthesize 1,4-diols by a hydroxyl-directed, aliphatic C-H bond functionalization reaction and is distinct from the synthesis of 1,3-diols from alcohols catalyzed by iridium. Mechanistic studies show that the rhodium-catalyzed silylation of alkyl C-H bonds occurs with a resting state and relative rates for elementary steps that are significantly different from those for the rhodium-catalyzed silylation of aryl C-H bonds. The resting state of the catalyst is a (Xantphos)Rh(I)(SiR
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