ArticleJournal of the American Chemical Society2015
Regiocontrol in catalytic reductive couplings through alterations of silane rate dependence.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Nickel-Catalyzed Defluorinative Coupling of Aliphatic Aldehydes with Trifluoromethyl Alkenes.ACS catalysis · 2022Article
- Case Study of N-Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Regiocontrol in the oxidative Heck reaction of indole by ligand-enabled switch of the regioselectivity-determining step.Chemical science · 2020Article
- Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles.Chemical reviews · 2020Review
- Alkenylation of C(spAngewandte Chemie (International ed. in English) · 2018Article
- NHC Ligands Tailored for Simultaneous Regio- and Enantiocontrol in Nickel-Catalyzed Reductive Couplings.Journal of the American Chemical Society · 2017Article
- Synthesis of Secondary and Tertiary Alkylboranes via Formal Hydroboration of Terminal and 1,1-Disubstituted Alkenes.Organic letters · 2016Article
- Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique Pathway for Cross-Electrophile Coupling.Journal of the American Chemical Society · 2016Article
- Ruthenium-Catalyzed Multicomponent Reactions: Access to α-Silyl-β-Hydroxy Vinylsilanes, Stereodefined 1,3-Dienes, and Cyclohexenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- Mechanistic Basis for Regioselection and Regiodivergence in Nickel-Catalyzed Reductive Couplings.Accounts of chemical research · 2015Article
- Nickel Catalysis: Synergy between Method Development and Total Synthesis.Accounts of chemical research · 2015Article
- Exo-selective reductive macrocyclization of ynals.Organic letters · 2015Article
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2 authors.
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Abstract
Combinations of ligand, reducing agent, and reaction conditions have been identified that allow alteration in the rate- and regioselectivity-determining step of nickel-catalyzed aldehyde-alkyne reductive couplings. Whereas previously developed protocols involve metallacycle-forming oxidative cyclization as the rate-determining step, this study illustrates that the combination of large ligands, large silanes, and elevated reaction temperature alters the rate- and regiochemistry-determining step for one of the two possible product regioisomers. These modifications render metallacycle formation reversible for the minor isomer pathway, and σ-bond metathesis of the metallacycle Ni-O bond with the silane reductant becomes rate limiting. The ability to tune regiocontrol via this alteration in reversibility of a key step allows highly regioselective outcomes that were not possible using previously developed methods.
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