ArticleJournal of the American Chemical Society2023
Remote Hydroamination of Disubstituted Alkenes by a Combination of Isomerization and Regioselective N-H Addition.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Cobalt-Catalyzed Radical Ligand Transfer (RLT) Enables Remote-Markovnikov Hydroamination of Alkenes.Angewandte Chemie (International ed. in English) · 2026Article
- Palladium-catalyzed cascade of aza-Wacker and Povarov reactions of aryl amines and 1,6-dienes for hexahydro-cyclopenta[b]quinoline framework.Nature communications · 2024Article
- 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
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
Remote hydrofunctionalizations of alkenes incorporate functional groups distal to existing carbon-carbon double bonds. While remote carbonylations are well-known, remote hydrofunctionalizations are most common for addition of relatively nonpolar B-H, Si-H, and C-H bonds with alkenes. We report a system for the remote hydroamination of disubstituted alkenes to functionalize an alkyl chain selectively at the subterminal, unactivated, methylene position. Critical to the high regioselectivity and reaction rates are the electronic properties of the substituent on the amine and the development of the ligand DIP-Ad-SEGPHOS by evaluating the steric and electronic effects of ligand modules on reactivity and selectivity. The remote hydroamination is compatible with a broad scope of alkenes and aminopyridines and enables the regioconvergent synthesis of amines from an isomeric mixture of alkenes. The products can be derivatized by nucleophilic aromatic substitution on the amino substituent with a variety of nucleophiles.
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Registered trials
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