ArticleJournal of the American Chemical Society2021
Ruthenium-Catalyzed Hydroamination of Unactivated Terminal Alkenes with Stoichiometric Amounts of Alkene and an Ammonia Surrogate by Sequential Oxidation and Reduction.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 45 citations in OpenAlex.
- Rhodium(III)-Catalyzed Remote Hydroamidation of Internal Alkenes via Chain Walking.ACS catalysis · 2023Article
- Photocatalytic Anti-Markovnikov Hydroamination of Alkenes with Primary Heteroaryl Amines.Journal of the American Chemical Society · 2023Article
- Progression of Hydroamination Catalyzed by Late Transition-Metal Complexes from Activated to Unactivated Alkenes.Accounts of chemical research · 2023Article
- Remote Hydroamination of Disubstituted Alkenes by a Combination of Isomerization and Regioselective N-H Addition.Journal of the American Chemical Society · 2023Article
- Rhodium(III)-Catalyzed Anti-Markovnikov Hydroamidation of Unactivated Alkenes Using Dioxazolones as Amidating Reagents.Journal of the American Chemical Society · 2022Article
- Enantioselective Giese Additions of Prochiral α-Amino Radicals.Journal of the American Chemical Society · 2022Article
- Rhodium-/Iridium-Catalyzed Hydroamination for the Synthesis of 1,2-, 1,3-, or 1,4-Diamines.ACS catalysis · 2022Article
- Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Hydroamination of alkenes catalyzed by transition-metal complexes is an atom-economical method for the synthesis of amines, but reactions of unactivated alkenes remain inefficient. Additions of N-H bonds to such alkenes catalyzed by iridium, gold, and lanthanide catalysts are known, but they have required a large excess of the alkene. New mechanisms for such processes involving metals rarely used previously for hydroamination could enable these reactions to occur with greater efficiency. We report ruthenium-catalyzed intermolecular hydroaminations of a variety of unactivated terminal alkenes without the need for an excess of alkene and with 2-aminopyridine as an ammonia surrogate to give the Markovnikov addition product. Ruthenium complexes have rarely been used for hydroaminations and have not previously catalyzed such reactions with unactivated alkenes. Identification of the catalyst resting state, kinetic measurements, deuterium labeling studies, and DFT computations were conducted and, together, strongly suggest that this process occurs by a new mechanism for hydroamination occurring by oxidative amination in concert with reduction of the resulting imine.
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