ArticleChemical science2021
Nickel-catalyzed reductive coupling of unactivated alkyl bromides and aliphatic aldehydes.
Article in Chemical science, 2021. 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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Who cites it
4 citing papers in PubMed.
- Catalytic 1,2-Migratory Insertion in a Bismuth Redox Platform: Reductive Arylation of Aldehydes.Angewandte Chemie (International ed. in English) · 2025Article
- Oxidative Cross Dehydrogenative Coupling ofJournal of the American Chemical Society · 2023Article
- Ni-Catalyzed Enantioselective Dialkyl Carbinol Synthesis via Decarboxylative Cross-Coupling: Development, Scope, and Applications.Journal of the American Chemical Society · 2022Article
- Nickel-Catalyzed Defluorinative Coupling of Aliphatic Aldehydes with Trifluoromethyl Alkenes.ACS catalysis · 2022Article
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Authors and funding
2 authors.
Funding
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Abstract
A mild, convenient coupling of aliphatic aldehydes and unactivated alkyl bromides has been developed. The catalytic system features the use of a common Ni(ii) precatalyst and a readily available bioxazoline ligand and affords silyl-protected secondary alcohols. The reaction is operationally simple, utilizing Mn as a stoichiometric reductant, and tolerates a wide range of functional groups. The use of 1,5-hexadiene as an additive is an important reaction parameter that provides significant benefits in yield optimizations. Initial mechanistic experiments support a mechanism featuring an alpha-silyloxy Ni species that undergoes formal oxidative addition to the alkyl bromide
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