ArticleJournal of the American Chemical Society2019
Nickel-Catalyzed Addition of Aryl Bromides to Aldehydes To Form Hindered Secondary Alcohols.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 93 citations in OpenAlex.
- Dynamic "Deactivation" mechanism enables epoxides ring-opening to prepare α-substituted alcohols.Nature communications · 2026Article
- Boron-Mediated Hydroalkylation of Unactivated Olefins: AnJournal of the American Chemical Society · 2026Article
- Enantioselective Synthesis of (+)-Auriculatol A.Journal of the American Chemical Society · 2025Article
- Catalytic 1,2-Migratory Insertion in a Bismuth Redox Platform: Reductive Arylation of Aldehydes.Angewandte Chemie (International ed. in English) · 2025Article
- Selectivity Effects of Hydrogen Acceptors and Catalyst Structures in Alcohol Oxidations Using (Cyclopentadienone)iron Tricarbonyl Compounds.The Journal of organic chemistry · 2025Article
- Electrochemical Enantioselective Nickel-Catalyzed Cross-Coupling of Aldehydes with Aryl Iodides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Effect of 6,6'-Substituents on Bipyridine-Ligated Ni Catalysts for Cross-Electrophile Coupling.ACS catalysis · 2024Article
- Progress toward the Total Synthesis of Nogalamycin Using a Benzyne Cycloaddition Strategy.The Journal of organic chemistry · 2024Article
- Interfacial Tuning of Electrocatalytic Ag Surfaces for Fragment-Based Electrophile Coupling.Nature catalysis · 2024Article
- First Reusable Catalyst for the Reductive Coupling Reaction of Organohalides with Aldehydes.ACS omega · 2023Article
- Nickel-Catalyzed Defluorinative Coupling of Aliphatic Aldehydes with Trifluoromethyl Alkenes.ACS catalysis · 2022Article
- Nickel-catalyzed reductive coupling of unactivated alkyl bromides and aliphatic aldehydes.Chemical science · 2021Article
- Deaminative Reductive Arylation Enabled by Nickel/Photoredox Dual Catalysis.Organic letters · 2019Article
- Rhodium-Catalyzed Aldehyde Arylation via Formate-Mediated Transfer Hydrogenation: Beyond Metallic Reductants in Grignard/Nozaki-Hiyami-Kishi-Type Addition.Journal of the American Chemical Society · 2019Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Transition-metal-catalyzed addition of aryl halides across carbonyls remains poorly developed, especially for aliphatic aldehydes and hindered substrate combinations. We report here that simple nickel complexes of bipyridine and PyBox can catalyze the addition of aryl halides to both aromatic and aliphatic aldehydes using zinc metal as the reducing agent. This convenient approach tolerates acidic functional groups that are not compatible with Grignard reactions, yet sterically hindered substrates still couple in high yield (33 examples, 70% average yield). Mechanistic studies show that an arylnickel, and not an arylzinc, adds efficiently to cyclohexanecarboxaldehyde, but only in the presence of a Lewis acid co-catalyst (ZnBr
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